Substituted Pyrimidine Ether Compounds and use thereof

ABSTRACT

The invention relates to substituted pyrimidine ether compounds having general formula I: 
     
       
         
         
             
             
         
       
     
     The groups are as defined as specification. 
     The compounds of formula I show high insecticidal activities for imagoes, larvae and nits of harmful acari and insects in the agricultural, civil and zoic fields, especially show excellent insecticidal activities for harmful acari such as  Tetranychus cinnabarinus . Good effects can be obtained at very low dose. The compounds also exhibit preferably fungicidal activity. Wherefore, the invention also comprises the uses of compounds of formula I as insecticides, acaricides and/or fungicides in agricultural and other fields.

FIELD OF THE INVENTION

The invention relates to insecticide, acaricide, fungicide. Specifically to substituted pyrimidine ether compounds and use thereof.

BACKGROUND OF THE INVENTION

Methoxyacrylate compounds are natural products and known with biological activity. Methoxyacrylate compounds with insecticidal and acaricidal activities were reported as follows: EP242081, EP299694, EP335519, US2006235075, etc. In addition, strobilurins containing pyrimidine moiety also show insecticidal, acaricidal and fungicidal activity:

The following compounds with insecticidal activity were known in U.S. Pat. No. 5,106,852:

Wherein: R₁ is selected from alkyl, cycloalkyl, haloalkyl, alkoxy, alkylthio, substituted or unsubstituted aryl.

The following compound with fungicidal activity was disclosed in U.S. Pat. No. 5,378,711:

The following compounds with acaricidal, fungicidal activity were known in U.S. Pat. No. 5,935,965:

The following compounds with insecticidal, fungicidal activity were known in U.S. Pat. No. 6,114,342:

The compounds disclosed above patents (applications) were similar to this invention, but there are some obvious differences in structures.

SUMMARY OF THE INVENTION

The aim of the present invention is to provide the substituted pyrimidine ether compounds with biological activity against all sorts of plant disease and insects at very low dosage and the compounds can be applied in agriculture to control disease and insects in plant.

Detailed description of the invention is as follows:

The present invention offeres substituted pyrimidine ether compounds having general formula I:

Wherein:

R₁ and R₂ may be the same or different, selected from H, CN, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₃-C₆cycloalkyl, C₁-C₁₂cyanoallyl, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₆dialkylamino, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkyl carbonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkoxyC₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonyl-C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, 2,3-(methylenedioxy)phenyl, 3,4-(methylenedioxy)phenyl, 2,3-(difluoromethylenedioxy)phenyl, 3,4-(difluoromethylenedioxy)phenyl, 2,3-dihydro-1H-indoline-4-yl, 5,6,7,8-tetrahydronaphthalene-1-yl, phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl or heteroaromatic rings; each phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl and heteroaromatic ring optionally substituted with 1-5 substituents independently selected from the group consisting of halogen, NO₂, CN, CONH₂, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylcarbonyl, C₁-C₂alkoxycarbonyl, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂ alkenyloxy, C₂-C₁₂haloalkenyloxy, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₂-C₁₂alkylnyloxy, C₂-C₁₂haloalkynyloxy, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₆dialkylamino, C₁-C₁₂alkylcarbonylamino, C₁-C₁₂haloalkylcarbonylamino or R₅;

Or NR₁R₂ can join together to form 5- or 6-membered ring;

R₃ and R₄ may be the same or different, selected from H, halogen, NO₂, CN, C₁-C₂haloalkyl, C₃-C₆cycloalkyl, C₁-C₁₂alkoxy; C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkyl sulfonyl, C₁-C₁₂ alkylcarbonyl, C₁-C₁₂ alkoxyC₁-C₁₂ alkyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonyl C₁-C₁₂ allyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, phenyl, benzyl or hetero aromatic rings; each phenyl, benzyl and heteroaromatic ring optionally substituted with 1-5 substituents independently selected from the group consisting of halogen, NO₂, CN, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₂allylthio, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl or R₃ and R₄ join together to form 5- or 6-membered ring;

R₅ is selected from phenyl, benzyl, phenoxy or benzyloxy; each phenyl, benzyl, phenoxy and benzyloxy optionally substituted with 1-5 substituents independently selected from the group consisting of halogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy or C₁-C₆haloalkoxy;

X is selected from O or S;

Q is selected from one of the following group:

Or their salts, or stereoisomer.

The preferred compounds of general formula I of this invention are:

R₁ and R₂ may be the same or different, selected from H, CN, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆cycloalkyl, C₁-C₆cyanoalkyl, C₁-C₆alkylamino, C₁-C₆haloalkylamino, C₂-C₆dialkylamino, C₁-C₆alkylthio, C₁-C₆alkylsulfonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkoxycarbonylC₁-C₆alkyl, C₁-C₆haloalkoxyC₁-C₆alkyl, 2,3-(methylenedioxy)phenyl, 3,4-(methylenedioxy)phenyl, 2,3-(difluoromethylenedioxy)phenyl, 3,4-(difluoromethylenedioxy)phenyl, 2,3-dihydro-1H-indoline-4-yl, 5,6,7,8-tetrahythonaphthalene-1-yl, 2,3-dihydro-1H-indoline-4-yl, 5,6,7,8-tetrahydronaphthalene-1-yl, phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl, pyridyl, thienyl, thiazolyl, benzothiazolyl or pyrazolyl; each phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl, pyridyl, thienyl, thiazolyl, benzothiazolyl and pyrazolyl optionally substituted with 1-5 substituents independently selected from the group consisting of halogen, NO₂, CN, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy; C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₃-C₆alkynyloxy, C₃-C₆haloalkynyloxy, C₁-C₆haloalkylthio, C₁-C₆haloalkylcarbonyl, C₁-C₆alkylamino, C₁-C₆haloalkylamino, C₂-C₆dialkylamino, C₁-C₆alkylcarbonylamino, C₁-C₆haloalkylcarbonylamino or R₅;

Or NR₁R₂ can join together to form morpholine, piperidine, pyrrolidine or piperazine;

R₃ and R₄ may be the same or different, selected from H, halogen, NO₂, CN, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkoxycarbonylC₁-C₆alkyl, C₁-C₆haloalkoxyC₁-C₆alkyl, phenyl, benzyl, pyridyl, thienyl, thiazolyl or pyrazolyl; each phenyl, benzyl, pyridyl, thienyl, thiazolyl and pyrazolyl optionally substituted with 1-3 substituents independently selected from the group consisting of halogen, NO₂, CN, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆ alkylcarbonyl, C₁-C₆alkoxycarbonyl or R₃ and R₄ join together to form 5- or 6-membered ring;

R₅ is selected from phenyl, benzyl, phenoxy or benzyloxy; each phenyl, benzyl, phenoxy and benzyloxy optionally substituted with 1-5 substituents independently selected from the group consisting of: halogen, C₁-C₄alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy or C₁-C₃haloalkoxy;

X is selected from O or S;

Q is selected from one of the following group: Q₁-Q₁₄; Or their salts are formed with hydrochlorides, phosphates, acetic acid, benzenesulfonic acid or oxalic acid.

Furthermore, the prepared compounds of general formula I of this invention are:

R₁ and R₂ may be the same or different, selected from H, CN, C₁-C₄alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃haloalkoxy, C₃-C₆cycloalkyl, C₁-C₃cyanoalkyl, C₁-C₆allylamino, C₁-C₃haloalkylamino, C₂-C₆dialkylamino, C₁-C₃ alkylsulfonyl, C₁-C₃ alkylcarbonyl, C₁-C₃alkoxyC₁-C₃ allyl, C₁-C₃alkoxycarbonyl, C₁-C₃haloalkoxyC₁-C₃alkyl, phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl, pyridyl, thienyl, thiazolyl or benzothiazolyl; each phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl, pyridyl, thienyl, thiazolyl and benzothiazolyl optionally substituted with 1-3 substituents independently selected from the group consisting of halogen, NO₂, CN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃ alkylthio, C₁-C₃alkylcarbonyl or C₁-C₃alkoxycarbonyl;

Or NR₁R₂ can join together to form morpholine, piperidine, pyrrolidine or piperazine;

R₃ and R₄ may be the same or different, selected from H, Cl, Br, NO₂, CN, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfonyl, C₁-C₃alkoxyC₁-C₃alkyl, C₁-C₃haloalkoxy C₁-C₃alkyl, phenyl, benzyl, pyridyl, thienyl, thiazolyl or pyrazolyl; each phenyl, benzyl, pyridyl, thienyl, thiazolyl and pyrazolyl optionally substituted with 1-3 substituents independently selected from the group consisting of halogen, NO₂, CN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃ alkylthio, C₁-C₃alkylcarbonyl, C₁-C₃ alkoxycarbonyl;

X is selected from O or S;

Q is selected from one of the following group: Q₁-Q₉;

Or their salts are formed with hydrochlorides, phosphates, acetic acid, benzenesulfonic acid or oxalic acid.

Even more prepared compounds of general formula I of this invention are:

R₁ is selected from H or C₁-C₄ alkyl;

R₂ is selected from H, CN, C₁-C₄alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₃-C₆cycloalkyl, C₁-C₃cyanoallyl, C₁-C₄alkylamino, C₁-C₃haloalkylamino, C₂-C₆dialkylamino, C₁-C₃ alkyl sulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxyC₁-C₂alkyl, phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl, pyridyl, thiazolyl or benzothiazolyl; each phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl, pyridyl, thiazolyl and benzothiazolyl optionally substituted with 1-3 substituents independently selected from the group consisting of halogen, NO₂, CN, C₁-C₃alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃haloalkoxy, C₁-C₃ alkylthio or C₁-C₃ alkoxycarbonyl;

Or NR₁R₂ can join together to form morpholine, piperidine, pyrrolidine or piperazine;

R₃ is selected from H, Cl, Br, F, C₁-C₄alkyl, C₃-C₆cycloalkyl, CF₃, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkoxyC₁-C₃alkyl, C₁-C₃haloalkoxyC₁-C₃alkyl, phenyl or pyridyl; each phenyl and pyridyl optionally substituted with 1-3 substituents independently selected from the group consisting of Cl, Br, F, NO₂, CN, C₁-C₃alkoxy or C₁-C₃haloalkoxy;

R₄ is selected from H, Cl, Br, F, OCH₃, OCF₃, SCH₃, SO₂CH₃, NHCH₃, CH₃, CN, OCH₂CF₃, CO₂C₂H₅, phenyl, benzyl or pyridyl; each phenyl, benzyl and pyridyl optionally substituted with 1-3 substituents independently selected from the group consisting of Cl, Br, F, NO₂, CN, C₁-C₃alkyl, CF₃, C₁-C₃alkoxy or C₁-C₃ alkylthio;

X is selected from O or S;

Q is selected from one of the following group: Q₁-Q₅; Or their salts are formed with hydrochlorides, phosphates, acetic acid, benzenesulfonic acid or oxalic acid.

The most prepared compounds of general formula I of this invention are:

R₁ is selected from H or C₁-C₄ alkyl;

R₂ is selected from H, CN, C₁-C₄alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₃-C₆cycloalkyl, phenyl, benzyl, pyridyl, thiazolyl or benzothiazolyl; each phenyl, benzyl, pyridyl, thiazolyl and benzothiazolyl optionally substituted with 1-3 substituents independently selected from the group consisting of Cl, Br, F, NO₂, CN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy or C₁-C₃haloalkoxy;

Or NR₁R₂ can join together to form morpholine, piperidine, pyrrolidine or piperazine;

R₃ is selected from H, Cl, Br, F, C₁-C₄alkyl, cyclopropyl, CF₃, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkoxyC₁-C₃alkyl or C₁-C₃haloalkoxy C₁-C₃alkyl;

R₄ is selected from H, Cl, Br, F, CH₃, OCH₃ or CN;

X is selected from O or S;

Q is selected from one of the following group: Q₁-Q₅.

The following is the meaning of terms in the general formula I:

Halogen or halo is fluorine, chlorine, bromine or iodine.

The alkyl is to be understood as meaning straightchain or branched alkyl, such as methyl, ethyl, propyl, isopropyl or tert-butyl.

The cycloalkyl is unsubstituted or optionally substituted cyclic alkyl, such as cyclopropyl, cyclopentyl or cyclohexyl. The substituted group is methyl or halogen.

The haloalkyl refers to straight or branched chain alkyl, in which hydrogen atoms may be all or partly substituted with halogen, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl.

The alkoxy refers to straight or branched chain alkyl, which is linked to the structure by oxygen atom.

The haloalkoxy refers to straight or branched chain alkoxy, in which hydrogen atoms may be all or partly substituted with halogen, such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy or trifluoroethoxy.

The alkylthio refers to straight or branched chain alkyl, which is linked to the structure by sulfur atom.

The haloalkylthio refers to straight or branched chain alkylthio, in which hydrogen atoms may be all or partly substituted with halogen, such as chloromethanethiol, dichloromethanethiol, trichloromethanethiol, fluoromethanethiol, difluoromethanethiol, trifluoromethanethiol, or chlorofluoromethanethiol.

The aryl and aryl in arylalkyl, aryloxy and aryloxyalkyl include phenyl or naphthyl.

The hetero aryl in this invention refers to five-membered ring or six-membered ring containing one or more N, O, S hetero atoms, such as pyridine, furan, pyrimidine, pyrazine, pyridazine, triazine, quinoline, thiazolyl, benzothiazolyl or benzofuran.

Because of the C═C or C═N links to different substituted group, the compounds of the invention may form geometrical isomers (the different isomers are respectively expressed with Z and E). Z isomer and E isomer and their mixtures in any proportion are included in the invention.

The group R₂ in general formula I refer to Table 1-8. When R₂ is pyridinyl, which substituted groups refer to Table 1-3. When R₂ is thiazolyl, which substituted groups refer to Table 4. When R₂ is phenyl, which substituted groups refer to Table 5. When R₂ is benzyl, which substituted groups refer to Table 6. When NR₁R₂ join together to form ring, the compounds refer to Table 7. When R₂ is other groups, which substituted groups refer to Table 8. The other groups in general formula I, such as R₁, R₃, R₄, X and Q, are defined as above.

TABLE 1

R R R R R H 3-Br 6-OCH₃ 3-CH₃-5-NO₂ 6-CH₃-3,5-2Br 3-CH₃ 4-Br 5-OCH₃ 4-CH₃-3-NO₂ 3-CONH₂-4,6-2Cl 4-CH₃ 5-Br 3,5-2Cl 4-CH₃-5-NO₂ 4-CH₃-5-NO₂-3-Br 5-CH₃ 6-Br 3,5-2Br 5-CH₃-5-NO₂ 3-CN-4,6-2Cl 6-CH₃ 5-I 4-CH₃-5-Br 6-CH₃-4-NO₂ 3-CN-4-CH₃-6-Cl 3-Cl 5-F 6-CH₃-5-CN 6-CH₃-5-NO₂ 3-CN-4-CF₃-6-Cl 4-Cl 6-F 3,5,6-3Cl 3-NO₂-5-Cl 4-CH₃-5-CN-6-Cl 5-Cl 3-CN 3-CO₂CH₃ 3-NO₂-5-Br 4-CF₃-5-CN-6-Cl 6-Cl 4-CN 5-CO₂CH₃ 5-NO₂-3-Br 3-CO₂CH₃-6-Cl 3-CF₃ 5-CN 3-OCH₂Ph 5-CH₂-3-Br 5-CO₂CH₃-6-Cl 4-CF₃ 6-CN 5-CF₃-3-Cl 6-CH₃-5-Br 5-CF₃-3,6-2Cl 5-CF₃ 3-NO₂ 5-CN-3-Cl 3-CH₃-5-Br 5-CF₃-6-Cl 6-CF₃ 5-NO₂ 5-CH₃-3-Cl 3-CF₃-6-Cl 3-CN-6-Cl

TABLE 2

R R R R R H 2-OCH₃ 4-CH₃-2-Cl 4-CF₃-2,6-2Cl 6-OPh-3,5-2CH₃-4-Cl 2-Cl 6-OCH₃ 5-CH₃-2-Cl 4-CH₃-2,6-2Cl 6-OCH₃-2-Cl 6-Cl 6-OPh 6-CH₃-2-Cl 6-OPh-4-Br 6-NHCH₃-5-Cl 2-Br 2,6-2Cl 2-OPh-6-Cl 2-OCH₂CF₃ 6-SO₂CH₃-5-Cl 6-Br 6-Ph 5,6-2Cl 2,5-2Cl 6-SPh-2,5-2Cl 4-CF₃ 4-CH₃ 6-CF₃

TABLE 3

R R R R R H 3-Cl 2-OCH₃ 2,6-2Cl 2-OCH₃-6-Cl 2-Cl 2-Br 2,6-2OCH₃ 6-OPh 2-NHCH₃-6-Cl

TABLE 4

R R R R R H 5-NO₂ 4-CO₂C₂H₅ 4-CH₃-5-COCH₃ 4-(Ph-4-Cl)-5-CO₂C₂H₅ 5-Cl 5-OPh 4-(Ph-3,4-2F) 4-CH₃-5-CO₂C₂H₅ 4,5-(CH═CH—CH═CH—) 5-CH₃ 5-OCH₃ 4-(Ph-4-Cl) 4-CF₃-5-CO₂C₂H₅ 4,5-(CH═CH—CH═CH—) 4-Cl 4,5-2Cl 4,5-(CH₂—)₃ 5-CH₃-4-CO₂C₂H₅ 4,5-(CH═CH—CH═CH—) 5-Br 4,5-2CH₃ 4,5-(CH₂—)₄ 5-Ph-4-CO₂C₂H₅ 4,5-(CMe═CH—CH═CH—) 4-CH₃ 4-C(CH₃)₃ 4-CF₃-5-CN 4-CH₃-5-CONHCH₃ 4,5-(CH═CMe—CH═CH—) 5-Ph 5-(Ph-4-Cl) 4-CH₂CO₂C₂H₅ 4-CF₃-5-CONHCH₃ 4,5-(C(OMe)═CH—CH═CH—) 4-Ph 4-(Ph-4-Br) 4-Ph-5-CO₂C₂H₅ 4,5-(CH═CH—CH═CH—) 4,5-(CH═C(OMe)—CH═CH—)

TABLE 5

R R R R R R R H 2-NO₂ 2-SO₂C₂H₅ 2,3-2F 2,3-2CH₃ 2-Cl-4-F 4-CH₃-2-Br 2-F 3-NO₂ 3-SO₂C₂H₅ 2,4-2F 2,4-2CH₃ 2-Cl-4-Br 4-CH₃-2-Cl 3-F 4-NO₂ 4-SO₂C₂H₅ 2,5-2F 2,5-2CH₃ 2-Cl-4-I 2,4,6-3CH₃ 4-F 2-SCF₃ 2-CO₂CH₃ 2,6-2F 2,6-2CH₃ 3-Cl-4-I 2,4,6-3C₂H₅ 2-Cl 3-SCF₃ 3-CO₂CH₃ 3,4-2F 3,4-2CH₃ 4-Cl-2-Br 2-NHCOCH₃ 3-Cl 4-SCF₃ 4-CO₂CH₃ 3,5-2F 3,5-2CH₃ 3,4,5-3F 3-NHCOCH₃ 4-Cl 2-OC₂H₅ 2-CO₂C₂H₅ 2,3-2Cl 2,3-2C₂H₅ 2,3,4-Cl 4-NHCOCH₃ 2-Br 3-OC₂H₅ 3-CO₂C₂H₅ 2,4-2Cl 2,4-2C₂H₅ 2,3,5-Cl 2-NHSO₂CH₃ 3-Br 4-OC₂H₅ 4-CO₂C₂H₅ 2,5-2Cl 2,5-2C₂H₅ 2,3,6-Cl 3-NHSO₂CH₃ 4-Br 2-COCH₃ 2-N(CH₃)2 2,6-2Cl 2,6-2C₂H₅ 2,4,5-Cl 4-NHSO₂CH₃ 2-I 3-COCH₃ 3-N(CH₃)2 3,4-2Cl 3,4-2C₂H₅ 2,4,6-Cl 2-(Ph-4-Cl) 3-I 4-COCH₃ 4-N(CH₃)2 3,5-2Cl 3,5-2C₂H₅ 3,4,5-Cl 3-(Ph-4-Cl) 4-I 2-CH₂Ph 2-N(C₂H₅)2 2,3-2Br 2,3-2CF₃ 2,3,4-3Br 4-(Ph-4-Cl) 2-CH₃ 3-CH₂Ph 3-N(C₂H₅)2 2,4-2Br 2,4-2CF₃ 2,3,5-3Br 2-CH(CH₃)₂ 3-CH₃ 4-CH₂Ph 4-N(C₂H₅)2 2,5-2Br 2,5-2CF₃ 2,3,6-3Br 3-CH(CH₃)₂ 4-CH₃ 2-C(CH₃)₃ 4-Ph 2,6-2Br 2,6-2CF₃ 2,4,5-3Br 4-CH(CH₃)₂ 2-C₂H₅ 3-C(CH₃)₃ 2-OPh 3,4-2Br 3,4-2CF₃ 2,4,6-3Br 2-CF₃-4-Cl 3-C₂H₅ 4-C(CH₃)₃ 3-OPh 3,5-2Br 3,5-2CF₃ 3,4,5-3Br 2-CF₃-4-Br 4-C₂H₅ 2-COCH₃ 4-OPh 2,3-2CN 2,6-2SCF₃ 4-CH₃-3-F 3-CF₃-4-NO₂ 2-CF₃ 3-COCH₃ 2,3-2OCH₃ 2,4-2CN 3,4-2SCF₃ 4-CH₃-3-Cl 3-CF₃-4-F 3-CF₃ 4-COCH₃ 2,4-2OCH₃ 2,5-2CN 3,5-2SCF₃ 4-CH₃-3-Br 3-CF₃-4-Cl 4-CF₃ 2-COC₂H₅ 2,5-2OCH₃ 2,6-2CN 2,3-2SCH₃ 2,4,6-3CF₃ 4-CF₃-2-NO₂ 2-OCH₃ 3-COC₂H₅ 2,6-2OCH₃ 3,4-2CN 2,4-2SCH₃ 2-CH₃-3-F 4-CF₃-2-Cl 3-OCH₃ 4-COC₂H₅ 3,4-2OCH₃ 3,5-2CN 2,5-2SCH₃ 2-CH₃-3-Cl 4-CF₃-2-Br 4-OCH₃ 2-SOCH₃ 3,5-2OCH₃ 2-F-4-Cl 2,6-2SCH₃ 2-CH₃-4-F 2-CH₃-5-NO₂ 2-SCH₃ 3-SOCH₃ 3-CONH₂ 2-F-4-Br 3,4-2SCH₃ 2-CH₃-4-Cl 2-CH₃-3-NO₂ 3-SCH₃ 4-SOCH₃ 4-CONH₂ 2-F-4-I 3,5-2SCH₃ 2-CH₃-4-Br 2-SCH₃-5-Cl 4-SCH₃ 2-SO₂CH₃ 2-OCH₂Ph 2-F-5-Cl 2,3-2OCF₃ 2-CH₃-5-F 4-SO₂CH₃-2Cl 2-OCF₃ 3-SO₂CH₃ 3-OCH₂Ph 3-F-5-Cl 2,4-2OCF₃ 2-CH₃-5-Cl 2-CH₃-4-NO₂ 3-OCF₃ 4-SO₂CH₃ 4-OCH₂Ph 4-F-3-Cl 2,5-2OCF₃ 2-CH₃-5-Br 2-CH₃-4-OCH₃ 4-OCF₃ 2-SOC₂H₅ 2,3-2NO₂ 4-F-6-Cl 2,6-2OCF₃ 2-CH₃-6-Cl 2-CH₃-6-C₂H₅ 2-CN 3-SOC₂H₅ 2,4-2NO₂ 2,3,4-3F 3,4-2OCF₃ 3-CH₃-2-Br 2-CH₃-6-NO₂ 3-CN 4-SOC₂H₅ 2,5-2NO₂ 2,3,5-3F 3,5-2OCF₃ 3-CH₃-4-Cl 2,4,6-3NO₂ 4-CN 2-OCHF₂ 2,6-2NO₂ 2,3,6-3F 2,3-2SCF₃ 3-CH₃-4-Br 2,3-2Cl-4-Br 2-Ph 3-OCHF₂ 3,4-2NO₂ 2,4,5-3F 2,4-2SCF₃ 3-CH₃-4-I 2,4-2F-6-Cl 3-Ph 4-OCHF₂ 3,5-2NO₂ 2,4,6-3F 2,5-2SCF₃ 2-CH₃-4-I 2-NO₂-4,6-2Br R R R R R 5-CF₃-2-Cl 5-CF₃-2-OCH₃ 4-CH₃-2,6-2Br 3-CH₃-4-NHCOCH₃ 2-NO₂-4-F 5-CF₃-2-Br 2-CF₃-4-NO₂ 5-CH₃-4-F-6-Cl 4-CH₃-3-NHSO₂CH₃ 2-NO₂-4-Cl 2-CN-3-F 2,4-2NO₂-6-Cl 4-C(CH₃)₃-2-Cl 4-CH₃-3-OCH₂Ph-6-Br 2-NO₂-4-Br 2-CN-3-Cl 2,4-2NO₂-6-Br 4-CF₃-2-Cl-6-Br 5-CH₃-2-OCH₃-4-Cl 2-NO₂-5-Cl 2-CN-4-NO₂ 2,3-2CH(CH₃)₂ 2-COOCH₃-4-Br 4-COCH₃-2,6-2Cl 3-NO₂-4-Cl 2-CN-4-Cl 2,4-2CH(CH₃)₂ 4-COOCH₃-2-Cl 5-CF₃-2-NHCOCH₃ 3-NO₂-4-Br 2-CN-4-Br 2,5-2CH(CH₃)₂ 4-COOCH₃-2-Br 2-CH₃-4-NO₂-6-Cl 4-NO₂-2-Cl 4-CN-2-CF₃ 2,6-2CH(CH₃)₂ 2,4,6-3CH(CH₃)₂ 2-CH₃-4-NO₂-6-Br 5-NO₂-2-Cl 4-CN-2-Cl 3,4-2CH(CH₃)₂ 2,4,6-3C(CH₃)₃ 2-CH₃-6-NO₂-4-Cl 5-NO₂-2-Br 4-CN-2-NO₂ 3,5-2CH(CH₃)₂ 2,3-2CH₃-6-NO₂ 2-CH₃-6-NO₂-4-Br 2-OCH₃-5-Cl 5-CH₃-2-F 2-NO₂-4-OCH₃ 2,4-2OCH₃-5-Cl 2,5-2OCH₃-4-NO₂ 4-OCH₃-3-F 4-CH₃-2-NO₂ 2-NO₂-4-OC₂H₅ 5-CONH₂-2-Cl 2,6-2CH₃-4-C(CH₃)₃ 4-OCH₃-3-Cl 4-CH₃-3-NO₂ 2,3-2C(CH₃)₃ 4-N(CH₃)₂-2-NO₂ 4-CF₃-2-NO₂-5-Cl 3-NO₂-4-F 5-CH₃-2-CN 2,4-2C(CH₃)₃ 5-N(CH₃)₂-2-NO₂ 4-CF₃-2-NO₂-6-Cl 2-OCF₃-4-CN 5-NO2-2-F 2,5-2C(CH₃)₃ 4,5-2CH₃-2-NO₂ 4-CF₃-2-NO₂-6-Br 2-OCF₃-4-Cl 2-CF₃-4,6-2Cl 2,6-2C(CH₃)₃ 2-NO₂-4-F-5-Cl 5-CH₃-2-CONH₂ 2-OCF₃-4-Br 2-CF₃-4,6-2Br 3,4-2C(CH₃)₃ 2-CN-4-NO₂-6-Cl 2-CH₃-5-CONH₂ 2-F-4,6-2Br 3-CH₃-2,6-2Cl 3,5-2C(CH₃)₃ 2-CN-4-NO₂-6-Br 5-NHCOCH₃-2-Cl 4-OCF₃-2-Cl 2-CH₃-4,6-2Br 4-SO₂NH₂ 2-OCH₂CH═CH₂ 4-O(CH₂)₂N(CH₃)₂ 4-OCF₃-2-Br 2,4,6-3OCH₃ 4-NO₂-2-OCH₃ 3-OCH₂CH═CH₂ 4-CH₃-3-OCH₂Ph 2,3,5,6-4F 3,4,5-3OCH₃ 2-CH₂CH═CH₂ 4-OCH₂CH═CH₂ 2-CH₂C(CH₃)═CH₂ 2-CN-4,6-2Cl 2,4,6-3SCH₃ 3-CH₂CH═CH₂ 2-OCH₂C≡CH 3-CH₂C(CH₃)═CH₂ 2-CN-4,6-2Br 2,4,6-3OCF₃ 4-CH₂CH═CH₂ 3-OCH₂C≡CH 4-CH₂C(CH₃)═CH₂ 4-CN-2,6-2Cl 2,4,6-3SCF₃ 2-C(CH₃)═CH₂ 4-OCH₂C≡CH 4-O(CH₂)₃CH₃-2-NO₂ 4-CF₃-2,6-2Cl 2-CH₂C≡CH 3-C(CH₃)═CH₂ 5-NO₂-2-OCH₃ 3-OCH₃-4-CO₂CH₃ 4-CF₃-2,6-2Br 3-CH₂C≡CH 4-C(CH₃)═CH₂ 5-CH₃-2-OCH₃ 2-CH(CH₃)CH₂CH(CH₃)₂ 2,3,4,5,6-5Cl 4-CH₂C≡CH 4-F-2,6-2Br 4-NO₂-2,6-2Cl 2,3-(CH₂CH₂CH₂—) 2,3-(OCF₂O—) 2-F-3-Cl 2,4-2F-6-Cl 4-OCF₃-2-NO₂ 2,3-(CH₂CH₂CH₂CH₂—) 2,3-(OCH₂O—) 3-CH₃-2-Cl 2-F-4-Cl-6-Br 6-NO₂-2,3,4-3F 4-NO₂-2,5-2Cl 3,4-(OCH₂O—) 4-O(CH₂)₃CH₃ 2,3,5,6-4F-4-CF₃ 4-NO₂-2,6-2Br 4-F-3-Cl-2,6-2Br 3,4-(OCF₂O—)

TABLE 6

The group R in table 6 is defined as above in table 5.

TABLE 7

—NR₁R₂

NHCH₂—≡—H NHCH₂—═—H

TABLE 8

R₂ H CH₃ C₂H₅

(CH₂)₂CH₃ CH(CH₃)₂ (CH₂)₃CH₃ C(CH₃)₃ (CH₂)₅CH₃ NH₂

(CH₂)₆CH₃ (CH₂)₇CH₃ OCH₃ OC₂H₅ OC(CH₃)₃ OCH₂CF₃ CN CH₂CN CH₂CH₂CN N(CH₃)₂

CF₃ CH₂CF₃ CF₂CF₃ CH₂CH₂Cl CH₂CH₂Br OCH(CH₃)₂ OCH₂CH₂Cl COPh-4-Cl COPh-4-NO₂ NHCH₃

COCH₂Cl COCH₂Br COPh COCH₃ COC₂H₅ CO₂CH₃ CO₂C₂H₅ SO₂CH₃ SO₂C₂H₅ NHPh NHCH₂CN NHCOCH₂CN

CH₂CO₂CH₃ CH₂CO₂C₂H₅ CH₂C(CH₃)₂CH₃ CH₂CH₂C(CH₃)₃ CH(CH₃)CH₂CH₃ CH₂CH(CH₃)₂ CH₂C(CH₃)₃ NHCH₂CF₃ NHPh-4-Cal CH(CH₃)CH₂CH(CH₃)₂ CONHCOPh CONHCOPh-2-Cl CONHCOPh-2,6-2Cl CONHCOPh-2,6-2F

The present invention is also explained by the following compounds in Table 9, but without being restricted thereby.

TABLE 9 I

No. X R₁ R₂ R₃ R₄ Q 1 O H CH₃ CH₃ H Q₁ 2 O H CH₃ CF₃ H Q₁ 3 O H CH₃ i-Pr H Q₁ 4 O H CH₃ t-Bu H Q₁ 5 O H CH₃ cyclopropyl H Q₁ 6 O H CH₃ Ph H Q₁ 7 O H CH₃ CH₃ CH₃ Q₁ 8 O H CH₃ CF₃ CH₃ Q₁ 9 O H CH₃ CF₃ Cl Q₁ 10 O H CH₃ i-Pr Cl Q₁ 11 O H CH₃ CH₃ OCH₃ Q₁ 12 O H CH₃ CF₃ OCH₃ Q₁ 13 O H CH₃ cyclopropyl OCH₃ Q₁ 14 O H CH₃ Ph OCH₃ Q₁ 15 O H CH₃ CH₃ SCH₃ Q₁ 16 O H CH₃ CF₃ SCH₃ Q₁ 17 O H CH₃ CH₃ NHCH₃ Q₁ 18 O H CH₃ CF₃ NHCH₃ Q₁ 19 O H Ph CH₃ H Q₁ 20 O H Ph CF₃ H Q₁ 21 O H H CH₃ H Q₁ 22 O H H CF₃ H Q₁ 23 O H Ph i-Pr H Q₁ 24 O H Ph t-Bu H Q₁ 25 O H Ph cyclopropyl H Q₁ 26 O H Ph Ph H Q₁ 27 O H Ph Ph-4-NO₂ H Q₁ 28 O H Ph CH₂Ph-4-OCH₃ H Q₁ 29 O H Ph Ph-2-CN H Q₁ 30 O H Ph Ph-4-Cl H Q₁ 31 O H Ph Cl H Q₁ 32 O H Ph Br H Q₁ 33 O H Ph OCH₃ H Q₁ 34 O H Ph OCH₂CF₃ H Q₁ 35 O H Ph SCH₃ H Q₁ 36 O H Ph NHCH₃ H Q₁ 37 O H Ph SO₂CH₃ H Q₁ 38 O H Ph NO₂ H Q₁ 39 O H Ph CN H Q₁ 40 O H Ph COC₂H₅ H Q₁ 41 O H Ph CH₃ CH₃ Q₁ 42 O H Ph CF₃ CH₃ Q₁ 43 O H Ph i-Pr CH₃ Q₁ 44 O H Ph t-Bu CH₃ Q₁ 45 O H Ph cyclopropyl CH₃ Q₁ 46 O H Ph Ph CH₃ Q₁ 47 O H Ph CH₃ Cl Q₁ 48 O H Ph CF₃ Cl Q₁ 49 O H Ph i-Pr Cl Q₁ 50 O H Ph t-Bu Cl Q₁ 51 O H Ph cyclopropyl Cl Q₁ 52 O H Ph Ph Cl Q₁ 53 O H Ph CH₃ Br Q₁ 54 O H Ph CF₃ Br Q₁ 55 O H Ph i-Pr Br Q₁ 56 O H Ph t-Bu Br Q₁ 57 O H Ph cyclopropyl Br Q₁ 58 O H Ph Ph Br Q₁ 59 O H Ph CH₃ OCH₃ Q₁ 60 O H Ph CF₃ OCH₃ Q₁ 61 O H Ph i-Pr OCH₃ Q₁ 62 O H Ph t-Bu OCH₃ Q₁ 63 O H Ph cyclopropyl OCH₃ Q₁ 64 O H Ph Ph OCH₃ Q₁ 65 O H Ph CH₃ SCH₃ Q₁ 66 O H Ph CF₃ SCH₃ Q₁ 67 O H Ph CH₃ NHCH₃ Q₁ 68 O H Ph CF₃ NHCH₃ Q₁ 69 O H Ph CH₃ SO₂CH₃ Q₁ 70 O H Ph CF₃ SO₂CH₃ Q₁ 71 O H Ph CF₃ NO₂ Q₁ 72 O H Ph CF₃ CN Q₁ 73 O H Ph CF₃ CH₂Cl Q₁ 74 O H Ph CF₃ CH₂CH₂Cl Q₁ 75 O H Ph CF₃ OCH₂CF₃ Q₁ 76 O H Ph CF₃ COC₂H₅ Q₁ 77 O H Ph CF₃ CO₂C₂H₅ Q₁ 78 O H Ph CF₃ CH₂OCH₂CF₃ Q₁ 79 O H Ph CF₃ Ph Q₁ 80 O H Ph CF₃ Ph-4-Cl Q₁ 81 O H Ph CF₃ Ph-2,4-2Cl Q₁ 82 O H Ph CF₃ Ph-4-CH₃ Q₁ 83 O H Ph CF₃ Ph-2-CH₃ Q₁ 84 O H Ph CF₃ Ph-4-NO₂ Q₁ 85 O H Ph CF₃ Ph-2,4-2SCH₃ Q₁ 86 O H Ph CF₃ Ph-4-OCH₃ Q₁ 87 O H Ph CF₃ Ph-2-CN Q₁ 88 O H Ph CF₃ CH₂Ph Q₁ 89 O H Ph CF₃ CH₂Ph-4-Cl Q₁ 90 O H Ph CF₃ CH₂Ph-2,4-2Cl Q₁ 91 O H Ph CF₃ CH₂Ph-4-NO₂ Q₁ 92 O H Ph CF₃ CH₂Ph-4-OCH₃ Q₁ 93 O H Ph CF₃ CH₂Ph-2-CN Q₁ 94 O H Ph CF₃

Q₁ 95 O H Ph CF₃

Q₁ 96 O H Ph CF₃

Q₁ 97 O H Ph CF₃

Q₁ 98 O H Ph CF₃

Q₁ 99 S H Ph CH₃ H Q₁ 100 S H Ph CF₃ H Q₁ 101 S H Ph cyclopropyl H Q₁ 102 S H Ph Ph H Q₁ 103 S H Ph Cl H Q₁ 104 S H Ph Br H Q₁ 105 O H Ph OCH₃ H Q₁ 106 S H Ph OCH₂CF₃ H Q₁ 107 S H Ph SCH₃ H Q₁ 108 S H Ph SO₂CH₃ H Q₁ 109 S H Ph CH₃ CH₃ Q₁ 110 S H Ph CF₃ CH₃ Q₁ 111 S H Ph i-Pr CH₃ Q₁ 112 S H Ph CH₃ Cl Q₁ 113 S H Ph CF₃ Cl Q₁ 114 S H Ph Ph Cl Q₁ 115 S H Ph CF₃ Br Q₁ 116 S H Ph CH₃ OCH₃ Q₁ 117 S H Ph CF₃ OCH₃ Q₁ 118 S H Ph CF₃ OCH₂CF₃ Q₁ 119 S H Ph CF₃ SCH₃ Q₁ 120 S H Ph CF₃ NHCH₃ Q₁ 121 S H Ph CH₃ SO₂CH₃ Q₁ 122 S H Ph CF₃ SO₂CH₃ Q₁ 123 S H Ph CF₃ CN Q₁ 124 O H CH₂CH₂CH₃ CF₃ H Q₁ 125 O H cyclopentanyl CF₃ H Q₁ 126 O H benzothiazol-2-yl CF₃ H Q₁ 127 O H thiazol-2-yl CF₃ H Q₁ 128 S H Ph CF₃ CO₂C₂H₅ Q₁ 129 S H Ph CF₃ Ph Q₁ 130 S H Ph CF₃ Ph-4-Cl Q₁ 131 S H Ph CF₃ Ph-4-NO₂ Q₁ 132 S H Ph CF₃ Ph-2,4-2SCH₃ Q₁ 133 S H Ph CF₃ Ph-4-OCH₃ Q₁ 134 S H Ph CF₃ Ph-2-CN Q₁ 135 S H Ph CF₃ CH₂Ph Q₁ 136 S H Ph CF₃ CH₂Ph-4-Cl Q₁ 137 S H Ph CF₃ CH₂Ph-2,4-2Cl Q₁ 138 S H Ph CF₃ CH₂Ph-4-NO₂ Q₁ 139 S H Ph CF₃ CH₂Ph-4-OCH₃ Q₁ 140 S H Ph CF₃ CH₂Ph-2-CN Q₁ 141 O H COCH₃ CF₃ H Q₁ 142 O H COCH₃ i-Pr H Q₁ 143 O H COCH₃ cyclopropyl H Q₁ 144 O H COCH₃ Ph H Q₁ 145 O H COCH₃ CH₃ CH₃ Q₁ 146 O H COCH₃ CF₃ CH₃ Q₁ 147 O H COCH₃ CH₃ Cl Q₁ 148 O H COCH₃ CF₃ Cl Q₁ 149 O H COCH₃ CH₃ OCH₃ Q₁ 150 O H COCH₃ CF₃ OCH₃ Q₁ 151 O H COCH₃ CF₃ OCH₂CF₃ Q₁ 152 O H COCH₃ CH₃ SCH₃ Q₁ 153 O H N═C(CH₃)₂ CF₃ H Q₁ 154 O H N═C(CH₃)Ph-4-Cl CF₃ H Q₁ 155 O H CH(CN)CH₃ CF₃ H Q₁ 156 O H COCH₂Cl CF₃ H Q₁ 157 O H COCH₂Cl CF₃ CH₃ Q₁ 158 O H COCH₂Cl CH₃ Cl Q₁ 159 O H COCH₂Cl CF₃ Br Q₁ 160 O H COCH₂Cl CF₃ OCH₃ Q₁ 161 O H COCH₂Cl CH₃ SCH₃ Q₁ 162 O H CO₂C₂H₅ CF₃ H Q₁ 163 O H CO₂C₂H₅ CF₃ CH₃ Q₁ 164 O H CO₂C₂H₅ CH₃ Cl Q₁ 165 O H CO₂C₂H₅ CF₃ Br Q₁ 166 O H CO₂C₂H₅ CF₃ OCH₃ Q₁ 167 O H CO₂C₂H₅ CH₃ SCH₃ Q₁ 168 O H CH₂CO₂C₂H₅ CF₃ H Q₁ 169 O H CH₂CO₂C₂H₅ CF₃ CH₃ Q₁ 170 O H SO₂CH₃ CF₃ H Q₁ 171 O (CH₂)₃CH₃ (CH₂)₃CH₃ CF₃ H Q₁ 172 O H SO₂CH₃ CH₃ Cl Q₁ 173 O H SO₂CH₃ CF₃ Br Q₁ 174 O H SO₂CH₃ CF₃ OCH₃ Q₁ 175 O H SO₂CH₃ CH₃ SCH₃ Q₁ 176 O CH₃ SO₂CH₃ CF₃ H Q₁ 177 O CH₃ SO₂CH₃ CF₃ CH₃ Q₁ 178 O CH₃ SO₂CH₃ CH₃ Cl Q₁ 179 O CH₃ SO₂CH₃ CF₃ Br Q₁ 180 O CH₃ SO₂CH₃ OCH₂CF₃ Br Q₁ 181 O H COPh CF₃ H Q₁ 182 O H COPh CF₃ CH₃ Q₁ 183 O H COPh-4-Cl CH₃ Cl Q₁ 184 O H COPh-4-NO₂ CF₃ Br Q₁ 185 O H CONHCOPh CF₃ H Q₁ 186 O H CONHCOPh CF₃ OCH₃ Q₁ 187 O H CONHCOPh-2,6-2F CF₃ SCH₃ Q₁ 188 O H CONHCOPh-2-Cl CF₃ H Q₁ 189 O C₂H₅ C₂H₅ CH₃ H Q₁ 190 O C₂H₅ C₂H₅ CF₃ H Q₁ 191 O H Ph-2-Cl CF₃ H Q₁ 192 O H Ph-2-CH₃ CF₃ H Q₁ 193 O H Ph-2-F CF₃ H Q₁ 194 O H Ph-2-C₂H₅ CF₃ H Q₁ 195 O H Ph-2-CH(CH₃)₂ CF₃ H Q₁ 196 O H Ph-2-OCH₃ CF₃ H Q₁ 197 O H Ph-2,3-(OCH₂O—) CF₃ H Q₁ 198 O C₂H₅ C₂H₅ CF₃ OCH₃ Q₁ 199 O C₂H₅ C₂H₅ CF₃ OCH₂CF₃ Q₁ 200 O C₂H₅ C₂H₅ CH₃ SCH₃ Q₁ 201 O C₂H₅ C₂H₅ CF₃ SCH₃ Q₁ 202 O C₂H₅ C₂H₅ CF₃ NHCH₃ Q₁ 203 O i-Pr Ph Ph H Q₁ 204 O i-Pr Ph CH₃ CH₃ Q₁ 205 O i-Pr Ph CF₃ H Q₁ 206 O i-Pr Ph CF₃ Cl Q₁ 207 O i-Pr Ph CH₃ OCH₃ Q₁ 208 O i-Pr Ph CF₃ OCH₃ Q₁ 209 O H NHCH₃ CF₃ H Q₁ 210 O H NHCH₂CF₃ CF₃ H Q₁ 211 O H OCH₃ CF₃ H Q₁ 212 O H OC₂H₅ CF₃ H Q₁ 213 O H NHPh CF₃ H Q₁ 214 O H NHPh-4-Cl CH₃ H Q₁ 215 O H NHCH₂Ph CF₃ H Q₁ 216 O H CN CF₃ H Q₁ 217 O H CH₂CN CF₃ H Q₁ 218 O H CH₂CH₂Cl CF₃ H Q₁ 219 O H N(CH₃)₂ CF₃ H Q₁ 220 O H CH₃ CH₃ H Q₂ 221 O H CH₃ CF₃ H Q₂ 222 O H CH₃ CH₃ CH₃ Q₂ 223 O H CH₃ CF₃ CH₃ Q₂ 224 O H CH₃ CF₃ Cl Q₂ 225 O H CH₃ i-Pr Cl Q₂ 226 O H CH₃ CF₃ OCH₃ Q₂ 227 O H CH₃ CF₃ SCH₃ Q₂ 228 O H CH₃ CH₃ NHCH₃ Q₂ 229 O H Ph CF₃ H Q₂ 230 O H Ph i-Pr H Q₂ 231 O H Ph t-Bu H Q₂ 232 O H Ph cyclopropyl H Q₂ 233 O H Ph Ph H Q₂ 234 O H Ph Ph-4-NO₂ H Q₂ 235 O H Ph CH₂Ph-4-OCH₃ H Q₂ 236 O H Ph Ph-4-Cl H Q₂ 237 O H Ph Cl H Q₂ 238 O H Ph Br H Q₂ 239 O H Ph OCH₃ H Q₂ 240 O H Ph SCH₃ H Q₂ 241 O H Ph NHCH₃ H Q₂ 242 O H Ph SO₂CH₃ H Q₂ 243 O H Ph NO₂ H Q₂ 244 O H Ph CN H Q₂ 245 O H Ph CF₃ CH₃ Q₂ 246 O H Ph i-Pr CH₃ Q₂ 247 O H Ph t-Bu CH₃ Q₂ 248 O H Ph t-Bu Cl Q₂ 249 O H Ph cyclopropyl Cl Q₂ 250 O H Ph CH₃ Br Q₂ 251 O H Ph CF₃ Br Q₂ 252 O H Ph i-Pr Br Q₂ 253 O H Ph CH₃ OCH₃ Q₂ 254 O H Ph CF₃ OCH₃ Q₂ 255 O H Ph CF₃ SCH₃ Q₂ 256 O H Ph CH₃ NHCH₃ Q₂ 257 O H Ph CF₃ NHCH₃ Q₂ 258 O H Ph CH₃ SO₂CH₃ Q₂ 259 O H Ph CF₃ SO₂CH₃ Q₂ 260 O H Ph CF₃ NO₂ Q₂ 261 O H Ph CF₃ CN Q₂ 262 O H Ph CF₃ CH₂Cl Q₂ 263 O H Ph CF₃ CH₂CH₂Cl Q₂ 264 O H Ph CF₃ OCH₂CF₃ Q₂ 265 O H Ph CF₃ COC₂H₅ Q₂ 266 O H Ph CF₃ CO₂C₂H₅ Q₂ 267 O H Ph CF₃ CH₂OCH₂CF₃ Q₂ 268 O H Ph CF₃ Ph Q₂ 269 O H Ph CF₃ Ph-4-Cl Q₂ 270 O H Ph CF₃ Ph-2,4-2Cl Q₂ 271 O H Ph CF₃ Ph-4-CH₃ Q₂ 272 O H Ph CF₃ Ph-2-CH₃ Q₂ 273 O H Ph CF₃ Ph-4-NO₂ Q₂ 274 O H Ph CF₃ Ph-2,4-2SCH₃ Q₂ 275 O H Ph CF₃ Ph-4-OCH₃ Q₂ 276 O H Ph CF₃ Ph-2-CN Q₂ 277 O H Ph CF₃ CH₂Ph Q₂ 278 O H Ph CF₃ CH₂Ph-4-Cl Q₂ 279 O H Ph CF₃ CH₂Ph-2,4-2Cl Q₂ 280 O H Ph CF₃ CH₂Ph-4-NO₂ Q₂ 281 S H Ph CH₃ H Q₂ 282 S H Ph CF₃ H Q₂ 283 S H Ph Br H Q₂ 284 S H Ph OCH₃ H Q₂ 285 S H Ph SCH₃ H Q₂ 286 S H Ph SO₂CH₃ H Q₂ 287 S H Ph CH₃ CH₃ Q₂ 288 S H Ph CF₃ CH₃ Q₂ 289 S H Ph i-Pr CH₃ Q₂ 290 S H Ph Ph Cl Q₂ 291 S H Ph CF₃ Br Q₂ 292 S H Ph CH₃ OCH₃ Q₂ 293 S H Ph CF₃ SO₂CH₃ Q₂ 294 S H Ph CF₃ CN Q₂ 295 S H Ph CF₃ CH₂Cl Q₂ 296 S H Ph CF₃ CH₂CH₂Cl Q₂ 297 S H Ph CF₃ OCH₂CF₃ Q₂ 298 S H Ph CF₃ COC₂H₅ Q₂ 299 S H Ph CF₃ CO₂C₂H₅ Q₂ 300 S H Ph CF₃ Ph Q₂ 301 S H Ph CF₃ Ph-4-Cl Q₂ 302 O H COCH₃ CF₃ H Q₂ 303 O H COCH₃ i-Pr H Q₂ 304 O H COCH₃ cyclopropyl H Q₂ 305 O H COCH₃ Ph H Q₂ 306 O H COCH₃ CH₃ CH₃ Q₂ 307 O H COCH₃ CF₃ OCH₃ Q₂ 308 O H COCH₃ CH₃ SCH₃ Q₂ 309 O H COCH₃ CF₃ SCH₃ Q₂ 310 O H COCH₃ CF₃ NHCH₃ Q₂ 311 O H COCH₂Cl CF₃ H Q₂ 312 O H COCH₂Cl CF₃ CH₃ Q₂ 313 O H CO₂C₂H₅ CF₃ H Q₂ 314 O H CO₂C₂H₅ CF₃ CH₃ Q₂ 315 O H CO₂C₂H₅ CH₃ Cl Q₂ 316 O H SO₂CH₃ CF₃ H Q₂ 317 O H SO₂CH₃ CF₃ CH₃ Q₂ 318 O H SO₂CH₃ CH₃ Cl Q₂ 319 O CH₃ SO₂CH₃ CF₃ H Q₂ 320 O CH₃ SO₂CH₃ CF₃ CH₃ Q₂ 321 O H COPh CF₃ H Q₂ 322 O H COPh CF₃ CH₃ Q₂ 323 O H COPh-4-Cl CH₃ Cl Q₂ 324 O H COPh-4-NO₂ CF₃ Br Q₂ 325 O H CONHCOPh CF₃ H Q₂ 326 O H CONHCOPh-2,6-2F CF₃ H Q₂ 327 O C₂H₅ C₂H₅ CH₃ H Q₂ 328 O C₂H₅ C₂H₅ CF₃ H Q₂ 329 O C₂H₅ C₂H₅ cyclopropyl H Q₂ 330 O C₂H₅ C₂H₅ Ph H Q₂ 331 O i-Pr Ph Ph H Q₂ 332 O i-Pr Ph CH₃ CH₃ Q₂ 333 O i-Pr Ph CF₃ Cl Q₂ 334 O H NHCH₃ CF₃ H Q₂ 335 O H NHCH₂CF₃ CF₃ H Q₂ 336 O H OCH₃ CF₃ H Q₂ 337 O H OC₂H₅ CF₃ H Q₂ 338 O H NHPh CF₃ H Q₂ 339 O H NHPh-4-Cl CH₃ H Q₂ 340 O H NHCH₂Ph CF₃ H Q₂ 341 O H CN CF₃ H Q₂ 342 O H CH₂CN CF₃ H Q₂ 343 O H CH₂CH₂Cl CF₃ H Q₂ 344 O H CH₂CH₂Cl CF₃ Br Q₂ 345 O H CH₃ CH₃ H Q₃ 346 O H CH₃ CF₃ H Q₃ 347 O H CH₃ CH₃ CH₃ Q₃ 348 O H CH₃ CF₃ CH₃ Q₃ 349 O H CH₃ CF₃ Cl Q₃ 350 O H CH₃ i-Pr Cl Q₃ 351 O H Ph CF₃ H Q₃ 352 O H Ph i-Pr H Q₃ 353 O H Ph Ph-4-NO₂ H Q₃ 354 O H Ph CH₂Ph-4-OCH₃ H Q₃ 355 O H Ph Ph-4-Cl H Q₃ 356 O H Ph Cl H Q₃ 357 O H Ph Br H Q₃ 358 O H Ph OCH₃ H Q₃ 359 O H Ph NHCH₃ H Q₃ 360 O H Ph SO₂CH₃ H Q₃ 361 O H Ph NO₂ H Q₃ 362 O H Ph CN H Q₃ 363 O H Ph CF₃ CH₃ Q₃ 364 O H Ph i-Pr CH₃ Q₃ 365 O H Ph t-Bu CH₃ Q₃ 366 O H Ph t-Bu Cl Q₃ 367 O H Ph cyclopropyl Cl Q₃ 368 O H Ph CF₃ OCH₃ Q₃ 369 O H Ph CF₃ SCH₃ Q₃ 370 O H Ph CH₃ NHCH₃ Q₃ 371 O H Ph CF₃ NHCH₃ Q₃ 372 O H Ph CH₃ SO₂CH₃ Q₃ 373 O H Ph CF₃ Ph-2-CH₃ Q₃ 374 O H Ph CF₃ Ph-4-NO₂ Q₃ 375 O H Ph CF₃ Ph-4-OCH₃ Q₃ 376 O H Ph CF₃ Ph-2-CN Q₃ 377 O H Ph CF₃ CH₂Ph Q₃ 378 O H Ph CF₃ CH₂Ph-4-Cl Q₃ 379 O H Ph CF₃ CH₂Ph-2,4-2Cl Q₃ 380 O H Ph CF₃ CH₂Ph-4-NO₂ Q₃ 381 S H Ph CH₃ H Q₃ 382 S H Ph CF₃ H Q₃ 383 S H Ph CF₃ CH₂CH₂Cl Q₃ 384 S H Ph CF₃ OCH₂CF₃ Q₃ 385 S H Ph CF₃ COC₂H₅ Q₃ 386 S H Ph CF₃ CO₂C₂H₅ Q₃ 387 S H Ph CF₃ Ph Q₃ 388 S H Ph CF₃ Ph-4-Cl Q₃ 389 O H COCH₃ CF₃ H Q₃ 390 O H COCH₃ i-Pr H Q₃ 391 O H COCH₃ cyclopropyl H Q₃ 392 O H COCH₃ Ph H Q₃ 393 O H COCH₃ CF₃ SCH₃ Q₃ 394 O H COCH₃ CF₃ NHCH₃ Q₃ 395 O H COCH₂Cl CF₃ H Q₃ 396 O H COCH₂Cl CF₃ CH₃ Q₃ 397 O H CO₂C₂H₅ CF₃ H Q₃ 398 O H CO₂C₂H₅ CF₃ CH₃ Q₃ 399 O H CO₂C₂H₅ CH₃ Cl Q₃ 400 O H SO₂CH₃ CF₃ H Q₃ 401 O H SO₂CH₃ CF₃ CH₃ Q₃ 402 O H SO₂CH₃ CH₃ Cl Q₃ 403 O CH₃ SO₂CH₃ CF₃ H Q₃ 404 O H COPh CF₃ CH₃ Q₃ 405 O H COPh-4-Cl CH₃ Cl Q₃ 406 O H COPh-4-NO₂ CF₃ Br Q₃ 407 O H CONHCOPh CF₃ H Q₃ 408 O H CONHCOPh-2,6-2F CF₃ H Q₃ 409 O C₂H₅ C₂H₅ CH₃ H Q₃ 410 O C₂H₅ C₂H₅ CF₃ H Q₃ 411 O C₂H₅ C₂H₅ cyclopropyl H Q₃ 412 O C₂H₅ C₂H₅ Ph H Q₃ 413 O i-Pr Ph Ph H Q₃ 414 O i-Pr Ph CH₃ CH₃ Q₃ 415 O H NHCH₂CF₃ CF₃ H Q₃ 416 O H OCH₃ CF₃ H Q₃ 417 O H NHPh-4-Cl CH₃ H Q₃ 418 O H NHCH₂Ph CF₃ H Q₃ 419 O H CN CF₃ H Q₃ 420 O H CH₃ CH₃ H Q₄ 421 O H CH₃ CF₃ H Q₄ 422 O H CH₃ CF₃ CH₃ Q₄ 423 O H CH₃ i-Pr Cl Q₄ 424 O H Ph CF₃ H Q₄ 425 O H Ph Ph-4-NO₂ H Q₄ 426 O H Ph CH₂Ph-4-OCH₃ H Q₄ 427 O H Ph Ph-4-Cl H Q₄ 428 O H Ph Cl H Q₄ 429 O H Ph Br H Q₄ 430 O H Ph OCH₃ H Q₄ 431 O H Ph CF₃ CH₃ Q₄ 432 O H Ph i-Pr CH₃ Q₄ 433 O H Ph t-Bu CH₃ Q₄ 434 O H Ph t-Bu Cl Q₄ 435 O H Ph cyclopropyl Cl Q₄ 436 O H Ph CF₃ OCH₃ Q₄ 437 O H Ph CF₃ NHCH₃ Q₄ 438 O H Ph CH₃ SO₂CH₃ Q₄ 439 O H Ph CF₃ Ph-2-CH₃ Q₄ 440 O H Ph CF₃ Ph-4-NO₂ Q₄ 441 O H Ph CF₃ CH₂Ph Q₄ 442 O H Ph CF₃ CH₂Ph-4-Cl Q₄ 443 S H Ph CF₃ H Q₄ 444 S H Ph CF₃ CH₂CH₂Cl Q₄ 445 S H Ph CF₃ OCH₂CF₃ Q₄ 446 S H Ph CF₃ COC₂H₅ Q₄ 447 S H Ph CF₃ CO₂C₂H₅ Q₄ 448 S H Ph CF₃ Ph Q₄ 449 S H Ph CF₃ Ph-4-Cl Q₄ 450 O H COCH₃ CF₃ SCH₃ Q₄ 451 O H COCH₃ CF₃ NHCH₃ Q₄ 452 O H COCH₂Cl CF₃ H Q₄ 453 O H COCH₂Cl CF₃ CH₃ Q₄ 454 O H CO₂C₂H₅ CF₃ H Q₄ 455 O H CO₂C₂H₅ CF₃ CH₃ Q₄ 456 O H CO₂C₂H₅ CH₃ Cl Q₄ 457 O H SO₂CH₃ CH₃ Cl Q₄ 458 O CH₃ SO₂CH₃ CF₃ H Q₄ 459 O H COPh CF₃ CH₃ Q₄ 460 O H COPh-4-Cl CH₃ Cl Q₄ 461 O H COPh-4-NO₂ CF₃ Br Q₄ 462 O H CONHCOPh CF₃ H Q₄ 463 O H CONHCOPh-2,6-2F CF₃ H Q₄ 464 O C₂H₅ C₂H₅ CH₃ H Q₄ 465 O C₂H₅ C₂H₅ CF₃ H Q₄ 466 O C₂H₅ C₂H₅ cyclopropyl H Q₄ 467 O C₂H₅ C₂H₅ Ph H Q₄ 468 O i-Pr Ph Ph H Q₄ 469 O i-Pr Ph CH₃ CH₃ Q₄ 470 O H NHCH₂CF₃ CF₃ H Q₄ 471 O H OCH₃ CF₃ H Q₄ 472 O H CH₃ CH₃ H Q₅ 473 O H CH₃ i-Pr Cl Q₅ 474 O H Ph CF₃ H Q₅ 475 O H Ph Br H Q₅ 476 O H Ph OCH₃ H Q₅ 477 O H Ph OCH₂CF₃ H Q₅ 478 O H Ph CF₃ CH₃ Q₅ 479 O H Ph i-Pr CH₃ Q₅ 480 O H Ph t-Bu Cl Q₅ 481 O H Ph cyclopropyl Cl Q₅ 482 O H Ph CF₃ OCH₃ Q₅ 483 O H Ph CF₃ NHCH₃ Q₅ 484 O H Ph CH₃ SO₂CH₃ Q₅ 485 O H Ph CF₃ Ph-2-CH₃ Q₅ 486 O H Ph CF₃ Ph-4-NO₂ Q₅ 487 O H Ph CF₃ CH₂Ph Q₅ 488 O H Ph CF₃ CH₂Ph-4-Cl Q₅ 489 S H Ph CF₃ H Q₅ 490 S H Ph CF₃ Ph Q₅ 491 S H Ph CF₃ Ph-4-Cl Q₅ 492 O H COCH₃ CF₃ SCH₃ Q₅ 493 O H COCH₃ CF₃ NHCH₃ Q₅ 494 O H COCH₂Cl CF₃ H Q₅ 495 O H COCH₂Cl CF₃ CH₃ Q₅ 496 O H CO₂C₂H₅ CF₃ H Q₅ 497 O H CO₂C₂H₅ CF₃ CH₃ Q₅ 498 O H SO₂CH₃ CH₃ Cl Q₅ 499 O CH₃ SO₂CH₃ CF₃ H Q₅ 500 O H COPh CF₃ CH₃ Q₅ 501 O H COPh-4-Cl CH₃ Cl Q₅ 502 O H COPh-4-NO₂ CF₃ Br Q₅ 503 O C₂H₅ C₂H₅ CF₃ H Q₅ 504 O C₂H₅ C₂H₅ cyclopropyl H Q₅ 505 O i-Pr Ph Ph H Q₅ 506 O i-Pr Ph CH₃ CH₃ Q₅ 507 O H NHCH₂CF₃ CF₃ H Q₅ 508 O H OCH₃ CF₃ H Q₆ 509 O H CH₃ CH₃ H Q₆ 510 O H CH₃ i-Pr Cl Q₆ 511 O H Ph CF₃ H Q₆ 512 O H Ph Br H Q₆ 513 O H Ph OCH₃ H Q₆ 514 O H Ph CF₃ CH₃ Q₆ 515 O H Ph cyclopropyl Cl Q₆ 516 O H Ph CF₃ OCH₃ Q₆ 517 S H Ph CF₃ H Q₆ 518 O H COCH₃ CF₃ SCH₃ Q₆ 519 O H COCH₂Cl CF₃ H Q₆ 520 O H COCH₂Cl CF₃ CH₃ Q₆ 521 O H SO₂CH₃ CH₃ Cl Q₆ 522 O H COPh CF₃ CH₃ Q₆ 523 O H COPh-4-Cl CH₃ Cl Q₆ 524 O C₂H₅ C₂H₅ CF₃ H Q₆ 525 O C₂H₅ C₂H₅ cyclopropyl H Q₆ 526 O i-Pr Ph Ph H Q₆ 527 O i-Pr Ph CH₃ CH₃ Q₆ 528 O H NHCH₂CF₃ CF₃ H Q₆ 529 O H OCH₃ CF₃ H Q₆ 530 O H OCH₃ CF₃ H Q₆ 531 O H CH₃ CH₃ H Q₆ 532 O H CH₃ i-Pr Cl Q₆ 533 O H Ph Br H Q₆ 534 O H Ph OCH₃ H Q₆ 535 O H Ph CF₃ CH₃ Q₆ 536 O H Ph i-Pr CH₃ Q₆ 537 O H Ph cyclopropyl Cl Q₆ 538 O H Ph CF₃ OCH₃ Q₆ 539 O H Ph CF₃ CH₂Ph-4-Cl Q₆ 540 O H COCH₃ CF₃ SCH₃ Q₆ 541 O H COCH₂Cl CF₃ H Q₆ 542 O H COCH₂Cl CF₃ CH₃ Q₆ 543 O H CO₂C₂H₅ CF₃ H Q₆ 544 O H SO₂CH₃ CH₃ Cl Q₆ 545 O H COPh CF₃ CH₃ Q₆ 546 O H COPh-4-Cl CH₃ Cl Q₆ 547 O C₂H₅ C₂H₅ CF₃ H Q₆ 548 O C₂H₅ C₂H₅ cyclopropyl H Q₆ 549 O i-Pr Ph CH₃ CH₃ Q₆ 550 O H NHCH₂CF₃ CF₃ H Q₆ 551 O H OCH₃ CF₃ H Q₆ 552 O H OCH₃ CF₃ H Q₇ 553 O H CH₃ CF₃ H Q₇ 554 O H CH₃ i-Pr Cl Q₇ 555 O H Ph CF₃ H Q₇ 556 O H Ph Br H Q₇ 557 O H Ph OCH₃ H Q₇ 558 O H Ph CF₃ CH₃ Q₇ 559 O H Ph cyclopropyl Cl Q₇ 560 O H SO₂CH₃ CH₃ Cl Q₇ 561 O H COPh CF₃ CH₃ Q₇ 562 O H COPh-4-Cl CH₃ Cl Q₇ 563 O C₂H₅ C₂H₅ CF₃ H Q₇ 564 O i-Pr Ph Ph H Q₇ 565 O i-Pr Ph CH₃ CH₃ Q₇ 566 O H NHCH₂CF₃ CF₃ H Q₇ 567 O H OCH₃ CF₃ H Q₇ 568 O H CH₃ CH₃ H Q₇ 569 O H CH₃ i-Pr Cl Q₇ 570 O H Ph i-Pr CH₃ Q₇ 571 O H Ph cyclopropyl Cl Q₇ 572 O H COCH₃ CF₃ SCH₃ Q₇ 573 O H COCH₂Cl CF₃ H Q₇ 574 O H SO₂CH₃ CH₃ Cl Q₇ 575 O H COPh CF₃ CH₃ Q₇ 576 O H COPh-4-Cl CH₃ Cl Q₇ 577 O C₂H₅ C₂H₅ CF₃ H Q₇ 578 O i-Pr Ph CH₃ CH₃ Q₇ 579 O H OCH₃ CF₃ H Q₇ 580 O H OCH₃ CF₃ H Q₈ 581 O H CH₃ CF₃ H Q₈ 582 O H Ph CF₃ H Q₈ 583 O H Ph Br H Q₈ 584 O H Ph cyclopropyl Cl Q₈ 585 O H SO₂CH₃ CH₃ Cl Q₈ 586 O H COPh CF₃ CH₃ Q₈ 587 O H COPh-4-Cl CH₃ Cl Q₈ 588 O C₂H₅ C₂H₅ CF₃ H Q₈ 589 O i-Pr Ph Ph H Q₈ 590 O i-Pr Ph CH₃ CH₃ Q₈ 591 O H NHCH₂CF₃ CF₃ H Q₈ 592 O H OCH₃ CF₃ H Q₈ 593 O H CH₃ i-Pr Cl Q₈ 594 O H Ph i-Pr CH₃ Q₈ 595 O H Ph cyclopropyl Cl Q₈ 596 O H COCH₃ CF₃ SCH₃ Q₈ 597 O H COPh-4-Cl CH₃ Cl Q₈ 598 O H OCH₃ CF₃ H Q₈ 599 O H CH₃ CF₃ H Q₉ 600 O H Ph CF₃ H Q₉ 601 O H Ph Br H Q₉ 602 O H SO₂CH₃ CH₃ Cl Q₉ 603 O H COPh CF₃ CH₃ Q₉ 604 O H COPh-4-Cl CH₃ Cl Q₉ 605 O C₂H₅ C₂H₅ CF₃ H Q₉ 606 O i-Pr Ph CH₃ CH₃ Q₉ 607 O H NHCH₂CF₃ CF₃ H Q₉ 608 O H CH₃ i-Pr Cl Q₉ 609 O H Ph i-Pr CH₃ Q₉ 610 O H Ph cyclopropyl Cl Q₉ 611 O H COPh-4-Cl CH₃ Cl Q₉ 612 O H OCH₃ CF₃ H Q₉ 613 O H CH₃ CF₃ H Q₁₀ 614 O H Ph CF₃ H Q₁₀ 615 O H Ph Br H Q₁₀ 616 O H COPh-4-Cl CH₃ Cl Q₁₀ 617 O C₂H₅ C₂H₅ CF₃ H Q₁₀ 618 O i-Pr Ph CH₃ CH₃ Q₁₀ 619 O H NHCH₂CF₃ CF₃ H Q₁₀ 620 O H CH₃ i-Pr Cl Q₁₀ 621 O H Ph cyclopropyl Cl Q₁₀ 622 O H COPh-4-Cl CH₃ Cl Q₁₀ 623 O H OCH₃ CF₃ H Q₁₀ 624 O H CH₃ CF₃ H Q₁₁ 625 O H Ph CF₃ H Q₁₁ 626 O H Ph Br H Q₁₁ 627 O H COPh-4-Cl CH₃ Cl Q₁₁ 628 O C₂H₅ C₂H₅ CF₃ H Q₁₁ 629 O i-Pr Ph CH₃ CH₃ Q₁₁ 630 O H NHCH₂CF₃ CF₃ H Q₁₁ 631 O H CH₃ i-Pr Cl Q₁₁ 632 O H Ph cyclopropyl Cl Q₁₁ 633 O H OCH₃ CF₃ H Q₁₁ 634 O H CH₃ CF₃ H Q₁₂ 635 O H Ph CF₃ H Q₁₂ 636 O H Ph Br H Q₁₂ 637 O H COPh-4-Cl CH₃ Cl Q₁₂ 638 O C₂H₅ C₂H₅ CF₃ H Q₁₂ 639 O i-Pr Ph CH₃ CH₃ Q₁₂ 640 O H NHCH₂CF₃ CF₃ H Q₁₂ 641 O H CH₃ i-Pr Cl Q₁₂ 642 O H Ph cyclopropyl Cl Q₁₂ 643 O H OCH₃ CF₃ H Q₁₂ 644 O H CH₃ CF₃ H Q₁₃ 645 O H Ph CF₃ H Q₁₃ 646 O H Ph Br H Q₁₃ 647 O H COPh-4-Cl CH₃ Cl Q₁₃ 648 O C₂H₅ C₂H₅ CF₃ H Q₁₃ 649 O i-Pr Ph CH₃ CH₃ Q₁₃ 650 O H NHCH₂CF₃ CF₃ H Q₁₃ 651 O H CH₃ i-Pr Cl Q₁₃ 652 O H Ph cyclopropyl Cl Q₁₃ 653 O H OCH₃ CF₃ H Q₁₃ 654 O H CH₃ CF₃ H Q₁₄ 655 O H Ph CF₃ H Q₁₄ 656 O H Ph Br H Q₁₄ 657 O H C₃H₇-i CF₃ H Q₁₄ 658 O H NHCH₂CF₃ CF₃ H Q₁₄ 659 O H Ph-2-Cl CH₃ Cl Q₁ 660 O H Ph-2-CH₃ CF₃ H Q₁ 661 O H Ph-3,5-2Cl CF₃ H Q₁ 662 O H Ph-2-CH₃-3-Cl CF₃ H Q₁ 663 O H C(CH₃)₃ CF₃ H Q₁ 664 O H Ph cyclopropyl H Q₄ 665 O H Ph cyclopropyl H Q₃ 666 O H Ph cyclopropyl H Q₅ 667 O H Ph CH₃ CH₃ Q₂ 668 O H Ph CH₃ CH₃ Q₄ 669 O H Ph CH₃ CH₃ Q₃ 670 O H Ph CH₃ CH₃ Q₅ 671 O H Ph CH₃ (CH₂)₃CH₃ Q₁ 672 O H Ph CH₃ (CH₂)₃CH₃ Q₂ 673 O H Ph CH₃ (CH₂)₃CH₃ Q₄ 674 O H Ph CH₃ (CH₂)₃CH₃ Q₃ 675 O H Ph CH₃ (CH₂)₃CH₃ Q₅ 676 O H Ph CH₃ H Q₂ 677 O H Ph CH₃ H Q₄ 678 O H Ph CH₃ H Q₃ 679 O H Ph CH₃ H Q₅ 680 O CH₃ CH₃ CF₃ H Q₁ 681 O H

CF₃ H Q₁ 682 O H CH(CH₃)₂ CF₃ H Q₁ 683 O CH₃ NH₂ CF₃ H Q₁ 684 O H Ph-4-CF₃ CF₃ H Q₁ 685 O H Ph-2,6-2F CF₃ H Q₁ 686 O H Ph-2,6-2Cl CF₃ H Q₁ 687 O H Ph-3-Cl CF₃ H Q₁ 688 O H Ph-4-OCH₃ CF₃ H Q₁ 689 O H Ph-4-F CF₃ H Q₁ 690 O H Ph-4-CH₃ CF₃ H Q₁ 691 O H 2-chloro-pyridin-3-yl CF₃ H Q₁ 692 O H cyclopropyl CF₃ H Q₁ 693 O H Ph-2,4-2CH₃ CF₃ H Q₁ 694 O H Ph2,3-2Cl CF₃ H Q₁ 695 O H Ph-2,5-2CH₃ CF₃ H Q₁ 696 O H CH₂Ph-2-Cl CF₃ H Q₁ 697 O H Ph-3,4-2CH₃ CF₃ H Q₁ 698 O H Ph-2,4,5-3CH₃ CF₃ H Q₁ 699 O H Ph-2-CH₃-4-Cl CF₃ H Q₁ 700 O H CH₂Ph CF₃ H Q₁ 701 O H cyclohexanyl CF₃ H Q₁ 702 O H C₂H₅ CF₃ H Q₁ 703 O H Ph-4-Cl CH₃ H Q₁ 704 O H Ph-4-Cl CF₃ H Q₁ 705 O H (CH₂)₃CH₃ CF₃ H Q₁ 706 O H CH₂CH(CH₃)₂ CF₃ H Q₁ 707 O H CH(CH₃)CH₂CH₃ CF₃ H Q₁ 708 O H CH₂C(CH₃)₃ CF₃ H Q₁ 709 O

CF₃ H Q₁ 710 O

CF₃ H Q₁ 711 O

CF₃ H Q₁ 712 O

CF₃ H Q₁ 713 O

CF₃ H Q₁ 714 O

CF₃ H Q₁ 715 O

CF₃ H Q₁ 716 O

CF₃ H Q₁ 717 O

CF₃ H Q₁ 718 O

CF₃ H Q₁

The present invention also includes preparation of the compounds having formula I:

When Q is chosen from one of Q₁, Q₂, Q₄, Q₆-Q₁₃, compounds having general formula I and their stereoisomers can be prepared by reaction of pyrimidine compounds containing hydroxy group having general formula III with halomethylbenzene having general formula IV at the present of base:

Wherein: L is leaving group, such as Cl or Br, other groups are as defined above. Intermediate of the general IV can be prepared according to known methods, refer to U.S. Pat. No. 4,723,034 and U.S. Pat. No. 5,554,578.

The reaction can be carried out in proper solvent, which may be selected from tetrahydrofuran, acetonitrile, toluene, xylene, benzene, DMF, DMSO, acetone or butanone and so on.

The proper base mentioned above may be selected from potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide and so on.

The proper temperature mentioned above is from room temperature to boiling point of solvent, normal temperature is from 20 to 100° C.

The reaction may be finished after 30 minutes to 20 hours, 1 hour to 10 hours in general.

The compounds having general formula I wherein Q represents Q₃, Q₅ or Q₁₄ can be prepared by reaction of the corresponding compounds wherein Q is selected from Q₂, Q₄ or Q₁₂ with methylamine aqueous.

Suitable salts of formula I were obtained from the compounds of formula I with 2-aminopyrimidine group reacting with inorganic acids, for example hydrochloride, phosphates and organic acids such as acetic acid, benzenesulfonic acid, oxalic acid.

Intermediate of the general formula III can be prepared by reaction of intermediate of the general formula II with ethyl 3-oxobutanoate, ethyl 4,4,4-trifluoro-3-oxobutanoate according to known methods, refer to GB1388402, U.S. Pat. No. 4,000,138, CH₃₉₅₃₈₅. Intermediate of the general formula II can be bought or prepared according to known methods, refer to EP310550, EP0655441.

Part of intermediates III are listed in table 10:

TABLE 10 Intermediate III III

No. R₁ R₂ R₃ R₄ m.p. (□) 1 H H CF₃ H 276-278 2 H Ph CH₃ H 258-260 3 H Ph CF₃ H 279-281 4 H Ph CH₃ CH₃ 282-284 5 H Ph CH₃ (CH₂)₃CH₃ 183-185 6 H Ph cyclopropyl H 112-115 7 H Ph 2-chloro-pyridin-5-yl H 204-205 8 H Ph 2-(2,2,2-trifluoroethoxy)pyridin-5-yl H 227-228 9 H Ph-4-Cl CH₃ H 251-253 10 H Ph-4-Cl CF₃ H 276-278 11 H Ph-4-Cl CF₃ Cl 12 H NH₂ CF₃ H 228-230 13 CH₃ CH₃ CF₃ H 174-176 14 CH₂CH₃ CH₂CH₃ CF₃ H 111-112 15 H CH(CH₃)₂ CF₃ H 176-178 16 CH₃ NH₂ CF₃ H 183-185 17 H Ph-4-CF₃ CF₃ H 213-215 18 H Ph-2,6-2F CF₃ H 158-160 19 H Ph-2,6-2Cl CF₃ H 216-218 20 H Ph-3-Cl CF₃ H 196-198 21 H Ph-4-OCH₃ CF₃ H 156-158 22 H Ph-4-CH₃ CF₃ H 207-209 23 H Ph-4-F CF₃ H 204-206 24 H 2-chloro-pyridin-3-yl CF₃ H >295 25 H cyclopropyl CF₃ H 181-183 26 H Ph-2-CH₃ CF₃ H 222-224 27 H Ph-2-Cl CF₃ H >290 28 H Ph-2-CH₃-3-Cl CF₃ H 234-236 29 H Ph-2,4-2CH₃ CF₃ H 230-232 30 H Ph-2,3-2Cl CF₃ H 264-266 31 H Ph-3,5-2Cl CF₃ H 287-288 32 H Ph-2,5-2CH₃ CF₃ H 216-218 33 H CH₂Ph-2-Cl CF₃ H 157-159 34 H Ph-3,4-2CH₃ CF₃ H 136-137 35 H Ph-2,4,5-3Cl CF₃ H 260-262 36 H Ph-2-CH₃-4-Cl CF₃ H 212-214 37 H CH₂Ph CF₃ H 152-154 38 H cyclohexanyl CF₃ H 234-235 39 H CH₃ CF₃ H 244-247 40 H CH₂CH₃ CF₃ H 192-194 41 H CH₂CH(CH₃)₂ CF₃ H 42 H CH(CH₃)CH₂CH₃ CF₃ H 43 C₄H₉-n C₄H₉-n CF₃ H 44 H CH₂CH₂CH₃ CF₃ H 45 H cyclopentanyl CF₃ H 168-170 46 H benzothiazol-2-yl CF₃ H 47 H thiazol-2-yl CF₃ H 48 H CH₂(CH₂)₂CH₃ CF₃ H 152-154 49 H CH₂C(CH₃)₃ CF₃ H 172-174 50 H C(CH₃)₃ CF₃ H 88-90 51 H N(CH₃)₂ CF₃ H 179-180 52 H OCH₃ CF₃ H 162-164 53 H OCH₂CH₃ CF₃ H 166-168 54 H CH(CN)CH₃ CF₃ H 55 H C(CN)(CH₃)₂ CF₃ H 56 H CN CF₃ H 164-166 57 H CH₂CN CF₃ H 58 H CH₂CH₂CN CF₃ H 59 H N═C(CH₃)₂ CF₃ H 60

CF₃ H 168-170 61

CF₃ H 261-263 62

CF₃ H 220-222

¹H-NMR (300 MHz, Intremediate No. internal standard TMS, solvent CDCl₃) 13 δ (ppm): 3.01 (s, 6H), 5.94 (s, 1H). 14 δ (ppm): 1.22 (t, 6H), 3.59 (q, 4H), 6.03 (s, 1H). 15 δ (ppm): 1.27 (d, 6H), 4.19 (m, 1H), 6.02 (s, 1H). 16 δ (ppm): 3.43 (s, 3H), 6.12 (s, 1H). 17 δ (ppm): 5.11 (s, 1H), 6.42 (s, 1H), 7.50 (m, 1H), 7.65 (m, 1H), 7.76 (m, 1H), 7.91 (m, 1H) (solvent DMSO).

The compounds having general formula I, which is exerted with respect to the adults, larvae and eggs of mites and insects which are harmful in the agricultural, have a high acaricidal and insecticidal activity, while the compounds also exhibit preferably fungicidal activity.

A further object of the present invention therefore relates to the use of the compounds having general formula I as acaricides, insecticides, and fungicides, both in agriculture and other fields. In particular, the compounds having general formula I are active against important species of tetranychidae (Tetranychus urticae, Tetranychus cinnabarinus, Panonychus ulmi, Panonychus citri, etc.), eriophyidae, tarsonemidae, etc. Additionally, some compounds in present invention also exhibit good fungicidal activity, which can be used to control of rice blast, tomato late blight, cucumber downy mildew, cucumber anthracnose, corn rust, wheat powdery mildew etc.

At the same time, the compounds having general formula I have a low toxicity with respect to many useful insects and mites, mammals, fish, birds, and have no phytotoxicity.

Thanks to their positive characteristics, they can be advantageously used in defending not only crops of agrarian and horticultural interest, but also domestic and breeding animals, as well as environments frequented by human beings, from harmful mites and insects.

For obtaining the desired effect, the quality of compounds can be varied in relation to various factors such as, the compound used, the crop to be preserved, the type of harmful organism, the degree of infestation, the climatic conditions, the method of application, the formulation adopted.

Doses of compounds ranging from 10 g to 5 kg per hectare generally provide a sufficient control.

A further object of the present invention also relates to a method for controlling mites and/or insects and/or phytopathogenic fungi in crops of agrarian and horticultural interest and/or on domestic and breeding animals and/or environments frequented by human beings, by the application of the compounds having general formula I. In particular, the quantity of compounds to be applied varies from 10 g to 5 kg per hectare.

For practical application in agriculture, it is usually beneficial to use compositions containing one or more compounds having general formula I.

A further object of the present invention therefore relates to acaricidal, insecticidal and fungicidal compositions containing compounds having general formula I as active principle and acceptable carrier in agriculture, the active component of the compositions is 0.5-90%.

Compositions can be used in the form of dry powders, wettable powders, emulsifiable concentrates, microemulsions, pastes, granulates, solutions, suspensions, etc.: the selection of the type of compositions depends on the specific application.

The compositions are prepared in the known way, for example by diluting or dissolving the active substance with a solvent medium and/or a solid diluent, optionally in the presence of surfactant

Solid diluents, or carriers which can be used are, for example: silica, kaolin, bentonite, talc, diatomite, dolomite, calcium carbonate, magnesia, chalk, clays, synthetic silicates, attapulgite, sepiolite.

Liquid diluents which can be used are, for example, besides water, aromatic organic solvents (xylols or mixtures of allylbenzols, chlorobenzene, etc.), paraffins (petroleum fractions), alcohols (methanol, propanol, butanol, octanol, glycerin, etc.), esters (ethyl acetate, isobutyl acetate, etc.), ketones (cyclohexanone, acetone, acetophenone, isophorone, ethylamylketone, etc.), amides (N, N-dimethylformamide, N-methylpyrrolidone, etc.).

Surfactant which can be used are salts of sodium, calcium, triethylamine or triethanolamine of alkylsulfonates, alkylarylsulfonates, polyethoxylated alkylphenols, polyethoxylated esters of sorbitol, ligninsulfonates, etc.

The compositions can also contain special additives for particular purposes, for example adhesive such as Arabic gum, polyvinyl alcohol, polyvinyl-pyrrolidone, etc.

The concentration of active principle in the above compositions can vary within a wide range depending on the active compound, the applications for which they are destined, the environmental conditions and the type of formulation adopted. In general the concentration of active principle ranges from 1 to 90%, preferably from 5 to 50%.

It is possible to add to the compositions, other active principles compatible with the compounds having general formula I according to requirement, such as, for example, other acaricides/insecticides, fungicides, phytoregulators, antibiotics, herbicides, fertilizers.

Several formulations of preparation methods, for example as follows:

The preparation of suspension concentrate: the common active component in formula is 5%-35%. With water as the medium, the compound, dispersing agent, suspending agent and antifreeze agent are added to sanding machine for grinding to make suspension concentrate.

The preparation of water emulsion: the compound, solvent and emulsifier are mixed together, to make a homogeneous oil phase. The water is mixed with antifreeze, as a homogeneous water phase. In the high-speed stirring, the aqueous phase added to the oil phase or oil phase is added to the aqueous phase, forming a good dispersion of the water emulsion. The active component of emulsions is generally 5%-15% in this invention. For the production of concentrated emulsions, the compounds of this invention are soluble in one or more of the mixed solvent, and then emulsifier is added to enhance dispersion effects in the water.

The preparation of wettable powder: the compound, surfactants and solid diluent are mixed well according to recipe requirements, after smashing through ultrafine pulverizer, that is the wettable powder products (for example, 10%-40%). For preparing the spraying wettable powder, the compounds of this invention can be mixed with solid power to form the mixture, such as clay, inorganic silicates, carbonates, as well as wetting agents, adhesives and/or dispersant agent.

The preparation of water dispersible granules: the compound and powdered solid diluents, wetting agents and adhesives are mixed to smash, kneaded together with water and added to the granulation 10-100 mesh machine for granulation, then by drying and sieving (at the scope screen). Also, the compounds, dispersants, wetting agents, disintegrants and solid diluent are added sanding machine, grinded with water for medium to produce suspension and then spray-drying granulation, usually the preparation of content is 20%-30% granular products.

DETAILED DESCRIPTION OF THE INVENTION

The following examples are illustrative of the present invention, but without being restricted thereby.

PREPARATION EXAMPLE Example 1 The preparation of compound 20

1.32 g of intermediate 3 (prepared according to Bioorganic & Medicinal Chemistry Letters, 2004, 14(17): 4449-4452) was dissolved in 30 ml of butanone, 1.6 g potassium carbonate was added to the solution, which is stirred to no bubble, then 1.25 g intermediate IV-1 was added, heated to reflux, after 8 hours, the reaction was traced by Thin-Layer Chromatography, then the salt was removed by filtration, washed by ethyl acetate, the combined organic extacts were concentrated at reduced pressure. The crude product was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1/5, as an eluent) and light yellow thick oil (compound 20) was obtained, which solidified to give 1.52 g product, m.p. 106-109° C.

¹H-NMR spectrum (300 MHz, internal standard: TMS, solvent CDCl₃) is as follows: δ(ppm): 3.70 (s, 3H), 3.78 (s, 3H), 5.33 (s, 2H), 6.48 (s, 1H), 7.07 (m, 1H), 7.20 (m, 1H), 7.34 (m, 4H), 7.49 (m, 211), 7.58 (s, 1H), 7.63 (m, 2H).

Example 2 The preparation of compound 680

0.50 g intermediate 13 was dissolved in 10 ml DMF, 0.67 g potassium carbonate was added to the solution, which is stirred at room temperature for half an hour, 0.53 g intermediate IV-2 was added, the reaction temperature was rised to 80°. 8 hours later, the reaction was traced by Thin-Layer Chromatography, after the reaction, the reaction mixture was poured into 30 ml saturated brine, extracted with ethyl acetate, the combined organic extracts were dried with sodium sulfate, and concentrated at reduced pressure. The crude product was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1/5, as an eluent) and light yellow thick oil (compound 680) was obtained, which solidified to give 0.31 g product, m.p 86-88° C.

¹H-NMR spectrum (300 MHz, internal standard:TMS, solvent CDCl₃) is as follows: δ(ppm): 3.16 (s, 6H), 3.67 (s, 3H), 3.80 (s, 3H), 5.30 (s, 2H), 6.21 (s, 1H), 7.20 (m, 1H), 7.35 (m, 2H), 7.47 (m, 1H), 7.57 (s, 1H).

Example 3 The preparation of compound 351

0.32 g compound 229 (the preparation is same with compound 20) was dissolved in 10 ml methanol, 2 ml 30% aqueous solution of methylamine was added, stirred at room temperature for 6 hours, the reaction was traced by Thin-Layer Chromatography, after the reaction, removed solvent at reduced pressure, the crude product was purified through silica gel column(ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1/3, as an eluent) and light yellow thick oil (compound 351) was obtained, which solidified to give 0.13 g product, m.p. 119-121° C.

¹H-NMR (300 MHz, internal standard:TMS, solvent CDCl₃) is as follows: δ(ppm): 2.98 (d, 3H), 3.96 (s, 3H), 5.17 (s, 2H), 6.46 (s, 1H), 7.02 (m, 2H), 7.38 (m, 5H), 7.73 (m, 2H), 8.22 (s, 1H).

Other compounds were prepared according the above examples.

Physical and chemical property and ¹HNMR spectrum (¹HNMR, 300 MHz, internal standard:TMS, solvent CDCl₃) of some compounds having the general formula I of this invention are as follows:

Compound 2: thick oil. δ(ppm): 2.98 (d, 3H), 3.69 (s, 3H), 3.81 (s, 3H), 5.28 (s, 2H), 6.28 (s, 1H), 7.19 (m, 1H), 7.34 (m, 2H), 7.49 (m, 1H), 7.58 (s, 1H).

Compound 19: thick oil. δ(ppm): 2.20 (3H, s), 3.71 (3H, s), 3.77 (3H, s), 5.33 (2H, s), 6.52 (1H, s), 7.11 (1H, m), 7.20 (1H, m), 7.39 (4H, m), 7.45 (2H, m), 7.59 (1H, s), 7.60 (2H, m).

Compound 22: thick oil. δ(ppm): 3.70 (s, 3H), 3.82 (s, 3H), 5.25 (s, 2H), 5.36 (s, 2H), 6.37 (s, 1H), 7.17 (m, 1H), 7.34 (m, 2H), 7.48 (m, 1H), 7.59 (s, 1H).

Compound 25: m.p. 54-56° C. δ(ppm): 1.01 (m, 2H), 1.15 (m, 2H), 1.83 (m, 1H), 3.65 (s, 3H), 3.78 (s, 3H), 5.27 (s, 2H), 6.06 (s, 1H), 7.01 (m, 1H), 7.18 (m, 1H), 7.33 (m, 4H), 7.51 (m, 1H), 7.57 (m, 1H), 7.62 (m, 2H).

Compound 41: m.p. 136-138° C. δ(ppm): 2.05 (s, 3H), 2.36 (s, 3H), 3.68 (s, 3H), 3.74 (s, 3H), 5.32 (s, 2H), 6.98 (m, 1H), 7.20 (m, 1H), 7.35 (m, 4H), 7.58 (m, 1H), 7.61 (s, 1H), 7.63 (m, 2H).

Compound 48: thick oil. δ(ppm): 3.74 (s, 3H), 3.84 (s, 3H), 4.49 (s, 2H), 7.13 (m, 1H), 7.33 (m, 5H), 7.54 (m, 2H), 7.60 (m, 1H), 7.71 (m, 1H).

Compound 109: m.p. 84-85° C. δ(ppm): 1.16 (t, 6H), 3.58 (q, 4H), 3.68 (s, 3H), 3.80 (s, 3H), 5.28 (s, 2H), 6.21 (s, 1H), 7.18 (m, 1H), 7.34 (m, 2H), 7.48 (m, 1H), 7.57 (s, 1H).

Compound 124: thick oil. δ(ppm): 0.97 (t, 3H), 1.61 (m, 2H), 3.36 (m, 2H), 3.69 (s, 3H), 3.80 (s, 3H), 4.30 (m, 1H), 5.29 (s, 2H), 6.27 (s, 1H), 7.17-7.20 (m, 1H), 7.33-7.36 (m, 2H), 7.48-7.51 (m, 1H), 7.58 (s, 1H).

Compound 125: thick oil. δ(ppm): 1.40-1.50 (m, 4H), 1.58-1.74 (m, 4H), 3.69 (s, 3H), 3.81 (s, 3H), 4.30-4.42 (m, 1H), 5.38 (s, 2H), 6.14 (s, 1H), 7.18-7.21 (m, 1H), 7.31-7.36 (m, 2H), 7.48-7.52 (m, 1H), 7.63 (s, 1H).

Compound 126: thick oil.

Compound 127: thick oil.

Compound 171: m.p. 82-84° C. δ(ppm): 0.96 (s, 9H), 3.26 (d, 2H), 3.69 (s, 3H), 3.80 (s, 3H), 5.30 (s, 2H), 6.26 (s, 1H), 7.17-7.20 (m, 1H), 7.33-7.38 (m, 2H), 7.48-7.51 (m, 1H), 7.58 (m, 1H).

Compound 211: m.p. 66-68° C.δ(ppm): 3.54 (s, 3H), 3.60 (s, 3H), 3.74 (s, 3H), 4.07 (m, 2H), 5.30 (s, 2H), 6.40 (s, 1H), 7.15-7.18 (m, 1H), 7.29-7.34 (m, 2H), 7.41-7.44 (m, 1H), 7.53 (s, 1H).

Compound 212: thick oil. δ(ppm): 0.96 (s, 9H), 3.26 (d, 2H), 3.69 (s, 3H), 3.80 (s, 3H), 5.30 (s, 2H), 6.26 (s, 1H), 7.17-7.20 (m, 1H), 7.33-7.38 (m, 2H), 7.48-7.51 (m, 1H), 7.58 (m, 1H).

Compound 216: thick oil. δ(ppm): 3.68 (s, 3H), 3.81 (s, 3H), 5.00 (s, 2H), 5.28 (s, 1H), 7.17-7.19 (m, 1H), 7.31-7.34 (m, 2H), 7.42 (m, 1H), 7.56 (s, 1H).

Compound 219: m.p. 116-118° C.

Compound 229: m.p. 124-126° C. δ(ppm): 3.88 (s, 3H), 4.01 (s, 3H,), 5.27 (s, 2H), 6.46 (s, 1H), 7.06 (m, 1H), 7.21 (m, 1H), 7.41 (m, 5H), 7.62 (m, 2H).

Compound 232: thick oil. δ(ppm): 0.93 (m, 2H), 1.14 (m, 2H), 1.86 (m, 1H), 3.85 (s, 3H), 4.00 (s, 3H), 5.23 (s, 2H), 6.03 (s, 1H), 7.02 (m, 1H), 7.19 (m, 1H), 7.30 (m, 2H), 7.40 (m, 2H), 7.48 (m, 1H), 7.62 (m, 2H).

Compound 424: m.p. 118-120° C. δ(ppm): 3.72 (s, 3H), 3.82 (s, 3H), 5.47 (s, 2H), 6.53 (s, 1H), 7.06 (m, 1H), 7.33 (m, 2H), 7.38 (m, 3H), 7.62 (m, 3H).

Compound 475: m.p. 117-119° C. δ(ppm): 2.93 (d, 3H), 3.65 (s, 3H), 5.45 (s, 2H), 6.50 (s, 1H), 7.02 (m, 1H), 7.30 (m, 5H), 7.49 (m, 1H), 7.69 (m, 2H), 8.05 (s, 1H).

Compound 659: m.p. 135-137° C. δ(ppm): 3.68 (s, 3H), 3.77 (s, 3H), 5.38 (s, 2H), 6.48 (s, 1H), 6.92 (m, 1H), 7.01 (m, 2H), 7.20 (m, 1H), 7.37 (m, 2H), 7.54 (m, 2H), 7.94 (s, 1H).

Compound 660: m.p. 118-120° C. δ(ppm): 2.35 (s, 3H), 3.66 (s, 3H), 3.74 (s, 3H), 5.26 (s, 2H), 6.45 (s, 1H), 7.08 (m, 2H), 7.16 (m, 1H), 7.22 (m, 2H), 7.34 (m, 2H), 7.38 (m, 1H), 7.54 (s, 1H)).

Compound 661: m.p. 147-149° C. δ(ppm): 3.75 (s, 3H), 3.83 (s, 3H), 5.25 (s, 2H), 6.55 (s, 1H), 7.01 (s, 1H), 7.26 (m, 1H), 7.34 (m, 2H), 7.44 (m, 2H), 7.63 (s, 1H), 7.67 (s, 1H).

Compound 662: m.p. 134-136° C. δ(ppm): 2.34 (s, 3H), 3.68 (s, 3H), 3.80 (s, 3H), 5.35 (s, 2H), 6.58 (s, 1H), 7.22 (m, 2H), 7.26 (m, 1H), 7.37 (m, 2H), 7.51 (m, 1H), 7.58 (s, 1H), 7.75 (s, 1H), 8.42 (d, 111).

Compound 663: thick oil. δ(ppm): 1.37 (d, 9H), 3.72 (s, 3H), 3.85 (s, 3H), 5.05 (s, 2H), 5.32 (s, 1H), 7.21 (m, 1H), 7.38 (m, 2H), 7.53 (m, 1H), 7.65 (s, 1H).

Compound 664: thick oil. δ(ppm): 1.00 (m, 2H), 1.15 (m, 2H), 1.85 (m, 1H), 3.73 (s, 3H), 3.80 (s, 3H), 5.40 (s, 2H), 6.10 (s, 1H), 7.00 (m, 1H), 7.29 (m, 2H), 7.37 (m, 3H), 7.56 (m, 1H), 7.60 (m, 2H).

Compound 665: m.p. 117-119° C. δ(ppm): 0.97 (m, 2H), 1.14 (m, 2H), 1.84 (m, 1H), 2.94 (d, 3H), 3.93 (s, 3H), 5.16 (s, 2H), 6.04 (s, 1H), 6.92 (m, 1H), 7.19 (m, 2H), 7.33 (m, 3H), 7.49 (m, 1H), 7.66 (m, 2H).

Compound 666: m.p. 122-124° C. δ(ppm): 1.00 (m, 2H), 1.17 (m, 2H), 1.85 (m, 1H), 2.91 (d, 3H), 3.63 (s, 3H), 5.43 (s, 2H), 6.00 (m, 1H), 6.10 (s, 1H), 6.95 (m, 1H), 7.33 (m, 5H), 7.61 (m, 1H), 7.65 (m, 2H).

Compound 667: m.p. 125-127° C. δ(ppm): 2.02 (s, 3H), 2.36 (s, 3H), 3.84 (s, 3H), 4.00 (s, 3H), 5.28 (s, 2H), 7.00 (m, 1H), 7.20 (m, 1H), 7.30 (m, 2H), 7.42 (m, 2H), 7.52 (m, 1H), 7.59 (m, 2H).

Compound 668: m.p. 102-104° C. δ(ppm): 2.09 (s, 3H), 2.36 (s, 3H), 3.72 (s, 3H), 3.79 (s, 3H), 5.48 (s, 2H), 7.00 (m, 1H), 7.32 (m, 2H), 7.38 (m, 3H), 7.59 (m, 3H).

Compound 669: m.p. 128-130° C. δ(ppm): 2.02 (s, 3H), 2.36 (s, 3H), 2.91 (d, 3H), 3.63 (s, 3H), 5.50 (s, 2H), 6.96 (m, 1H), 7.34 (m, 5H, 7.55 (m, 1H), 7.64 (m, 2H).

Compound 670: m.p. 138-140° C. δ(ppm): 2.09 (s, 3H), 2.37 (s, 3H), 2.90, (d, 3H), 3.92 (s, 3H), 5.24 (s, 2H), 5.98 (m, 1H), 6.99 (m, 1H), 7.24 (m, 2H), 7.38 (m, 4H), 7.64 (m, 2H).

Compound 671: m.p. 85-88° C. δ(ppm): 0.91 (t, 3H), 1.40 (m, 4H), 2.40 (s, 3H), 2.53 (t, 2H), 3.69 s, 3H), 3.75 (s, 3H), 5.24 (s, 2H), 7.01 (m, 1H), 7.32 (m, 5H), 7.58 (m, 3H), 7.61 (s, 1H).

Compound 672: m.p. 84-85° C. δ(ppm): 0.95 (t, 3H), 1.38 (m, 4H), 2.38 (s, 3H), 2.51 (t, 2H), 3.69 (s, 3H), 3.81 (s, 3H), 5.27 (s, 2H), 7.00 (m, 1H), 7.26 (m, 5H), 7.55 (m, 1H), 7.73 (m, 2H).

Compound 673: thick oil. δ(ppm): 0.93 (t, 3H), 1.41 (m, 4H), 2.40 (s, 3H), 2.56 (t, 2H), 3.73 (s, 3H), 3.81 (s, 3H), 5.47 (s, 2H), 6.98 (m, 1H), 7.28 (m, 2H), 7.37 (m, 3H), 7.58 (m, 3H).

Compound 674: m.p. 110-112° C. δ(ppm): 0.93 (t, 3H), 1.41 (m, 4H), 2.36 (s, 3H), 2.51 (t, 2H), 3.93 (d, 3H), 3.91 (s, 3H), 5.21 (s, 2H), 6.98 (m, 1H), 7.38 (m, 6H), 7.67 (m, 2H).

Compound 675: m.p. 101-103° C. δ(ppm): 0.93 (t, 3H), 1.41 (m, 4H), 2.43 (s, 3H), 2.52 (t, 2H), 2.90 (d, 3H), 3.60 (s, 3H, CH₃), 5.54 (s, 2H), 7.00 (m, 1H), 7.38 (m, 5H), 7.50 (m, 1H), 7.61 (m, 2H).

Compound 676: thick oil. δ(ppm): 2.33 (s, 3H), 3.85 (s, 3H), 4.01 (s, 3H), 5.25 (s, 2H), 6.03 (s, 1H), 7.00 (m, 1H), 7.25 (m, 5H), 7.45 (m, 1H), 7.59 (m, 2H).

Compound 677: m.p. 89-91° C. δ(ppm): 2.35 (s, 3H), 2.73 (s, 3H), 3.79 (s, 3H), 5.45 (s, 2H), 6.10 (s, 1H), 7.00 (m, 1H), 7.35 (m, 5H), 7.58 (m, 1H), 7.61 (m, 2H).

Compound 678: m.p. 130-132° C. δ(ppm): 2.33 (s, 3H), 2.93 (d, 3H), 3.93 (s, 3H), 5.19 (s, 2H), 6.04 (s, 1H), 7.00 (m, 1H), 7.35 (m, 5H), 7.42 (m, 1H), 7.64 (m, 2H).

Compound 679: m.p. 130-131° C. δ(ppm): 2.36 (s, 3H), 2.90 (d, 3H), 3.63 (s, 3H), 5.47 (s, 2H), 6.10 (s, 1H), 7.00 (m, 1H), 7.35 (m, 5H), 7.50 (m, 1H), 7.67 (m, 2H).

Compound 681: m.p. 80-83° C. δ(ppm): 3.75 (s, 3H), 3.89 (s, 3H), 5.32 (s, 2H), 6.72 (s, 1H), 7.00 (m, 2H), 7.20 (m, 1H), 7.35 (m, 2H), 7.47 (m, 2H), 7.64 (s, 1H).

Compound 682: thick oil. δ(ppm): 1.24 (d, 6H), 3.71 (s, 3H), 3.81 (s, 3H), 4.10 (d, 1H), 5.28 (s, 2H), 6.27 (s, 1H), 7.20 (m, 1H), 7.34 (m, 2H), 7.46 (m, 1H), 7.58 (s, 1H).

Compound 683: thick oil. δ(ppm): 3.42 (s, 3H), 3.53 (s, 3H), 3.67 (s, 3H), 5.34 (s, 2H), 6.34 (s, 1H), 7.18 (m, 1H), 7.33 (m, 2H), 7.44 (m, 1H), 7.58 (s, 1H).

Compound 684: m.p. 149-151° C. δ(ppm): 3.74 (s, 3H), 3.81 (s, 3H), 5.35 (s, 2H), 6.57 (s, 1H), 7.21 (m, 1H), 7.35 (m, 2H), 7.48 (m, 1H), 7.57 (m, 2H), 7.62 (s, 1H), 7.78 (m, 2H).

Compound 685: m.p. 146-149° C. δ(ppm): 3.67 (s, 3H), 3.75 (s, 3H), 5.16 (s, 2H), 6.48 (s, 1H), 6.71 (m, 1H), 7.00 (m, 2H), 7.18 (m, 2H), 7.32 (m, 2H), 7.54 (s, 1H).

Compound 686: m.p. 184-186° C. δ(ppm): 3.64 (s, 3H), 3.70 (s, 3H), 5.10 (s, 2H), 6.46 (s, 1H), 6.93 (m, 1H), 7.25 (m, 4H), 7.43 (m, 2H), 7.53 (s, 1H).

Compound 687: m.p. 125-126° C. δ(ppm): 3.73 (s, 3H), 3.81 (s, 3H), 5.31 (s, 2H), 6.52 (s, 1H), 7.00 (m, 1H), 7.20 (m, 2H), 7.35 (m, 2H), 7.50 (m, 2H), 7.61 (s, 1H), 8.79 (m, 1H).

Compound 688: m.p. 137-139° C. δ(ppm): 3.70 (s, 3H), 3.78 (s, 3H), 3.81 (s, 3H), 5.29 (s, 2H), 6.43 (s, 1H), 6.90 (m, 2H), 7.20 (m, 2H), 7.35 (m, 2H), 7.52 (m, 2H), 7.58 (s, 1H).

Compound 689: m.p. 136-138° C. δ(ppm): 3.72 (s, 3H), 3.80 (s, 3H), 5.30 (s, 2H), 6.49 (s, 1H), 7.03 (m, 2H), 7.20 (m, 1H), 7.35 (m, 2H), 7.47 (m, 1H), 7.57 (m, 2H), 7.60 (s, 1H).

Compound 690: m.p. 140-142° C. δ(ppm): 2.33 (s, 3H), 3.70 (s, 3H), 3.78 (s, 3H), 5.31 (s, 2H), 6.45 (s, 1H), 7.14 (m, 2H), 7.20 (m, 1H), 7.35 (m, 2H), 7.50 (m, 3H), 7.58 (s, 1H).

Compound 691: m.p. 128-130° C. δ(ppm): 3.69 (s, 3H), 3.81 (s, 3H), 5.36 (s, 2H), 6.61 (s, 1H), 7.03 (m, 2H), 7.20 (m, 1H), 7.29 (m, 1H), 7.38 (m, 2H), 7.60 (s, 1H), 7.67 (s, 1H), 8.82 (m, 1H).

Compound 692: m.p. 94-96° C. δ(ppm): 0.55 (m, 2H), 0.80 (m, 2H,), 3.69 (s, 3H), 3.81 (s, 3H), 5.26 (s, 2H), 6.33 (s, 1H), 7.19 (m, 1H), 7.35 (m, 2H), 7.56 (m, 1H), 7.58 (s, 1H).

Compound 693: m.p. 126-127° C. δ(ppm): 2.29 (s, 3H), 2.33 (s, 3H), 3.66 (s, 3H), 3.74 (s, 3H), 5.23 (s, 2H), 6.4 (s, 1H), 6.89 (s, 1H), 7.05 (m, 2H), 7.17 (m, 1H), 7.33 (m, 3H), 7.54 (s, 1H), 7.70 (d, 1H).

Compound 694: m.p. 134-136° C. δ(ppm): 3.68 (s, 3H), 3.80 (s, 3H), 5.35 (s, 2H), 6.58 (s, 1H), 7.22 (m, 2H), 7.26 (m, 1H), 7.37 (m, 2H), 7.51 (m, 1H), 7.58 (s, 1H), 7.75 (s, 1H), 8.42 (d, 1H).

Compound 695: oil. δ(ppm): 2.29 (s, 3H), 2.32 (s, 3H), 3.64 (s, 3H), 3.71 (s, 3H), 5.25 (s, 2H), 6.43 (s, 1H), 6.91 (m, 2H), 7.13 (m, 2H), 7.33 (m, 2H), 7.53 (s, 1H, CH), 7.72 (s, 1H).

Compound 696: m.p. 133-135° C. δ(ppm): 3.66 (s, 3H), 3.77 (s, 3H), 4.70 (d, 2H), 5.26 (s, 2H), 6.32 (s, 1H), 7.20 (m, 3H), 7.35 (m, 5H), 7.57 (s, 1H).

Compound 697: m.p. 142-144° C. δ(ppm): 2.23 (s, 3H), 2.25 (s, 3H), 3.70 (s, 3H), 3.78 (s, 3H), 5.26 (s, 2H), 6.44 (s, 1H), 7.11 (m, 1H), 7.20 (m, 2H), 7.35 (m, 2H), 7.40 (m, 1H), 7.48 (s, 1H), 7.53 (s, 1H).

Compound 698: thick oil. δ(ppm): 3.63 (s, 3H), 3.72 (s, 3H), 4.80 (s, 2H), 6.37 (s, 1H), 6.95 (m, 2H), 7.06 (m, 2H), 7.40 (m, 1H), 7.49 (m, 1H), 7.58 (s, 1H).

Compound 699: m.p. 138-140° C. δ(ppm): 2.31 (s, 3H), 3.67 (s, 3H), 3.76 (s, 3H), 5.25 (s, 2H), 6.48 (s, 1H), 6.92 (d, 1H), 7.20 (m, 3H), 7.35 (m, 2H), 7.40 (m, 1H), 7.55 (s, 1H), 7.82 (d, 1H).

Compound 700: m.p. 122-124° C. δ(ppm): 3.64 (s, 3H), 3.75 (s, 3H), 4.60 (d, 2H), 5.22 (s, 2H), 6.32 (s, 1H), 7.19 (m, 1H), 7.33 (m, 7H), 7.42 (m, 1H), 7.58 (s, 1H).

Compound 701: m.p. 136-137° C. δ(ppm): 1.30 (m, 6H), 1.68 (m, 4H), 2.01 (m, 1H), 3.69 (s, 3H), 3.81 (s, 3H), 5.24 (s, 2H), 6.24 (s, 1H), 7.19 (m, 1H), 7.35 (m, 2H), 7.49 (m, 1H), 7.58 (s, 1H).

Compound 702: thick oil. δ(ppm): 1.23 (t, 3H), 3.43 (q, 2H), 3.69 (s, 3H), 3.81 (s, 3H), 5.28 (s, 2H), 6.28 (s, 1H), 7.20 (m, 1H), 7.34 (m, 2H), 7.48 (m, 1H), 7.58 (s, 1H).

Compound 703: thick oil. δ(ppm): 2.34 (s, 3H), 3.70 (s, 3H), 3.78 (s, 3H), 5.27 (s, 2H), 7.19 (m, 1H,), 7.24 (m, 2H), 7.34 (m, 2H), 7.49 (m, 1H), 7.55 (m, 2H), 7.58 (m, 1H).

Compound 704: thick oil. δ(ppm): 3.72 (s, 3H), 3.78 (s, 3H), 5.31 (s, 2H), 6.51 (s, 1H), 7.19 (m, 1H), 7.29 (m, 2H), 7.35 (m, 2H), 7.48 (m, 1H), 7.57 (m, 2H), 7.60 (m, 1H).

Compound 705: thick oil. δ(ppm): 0.97 (t, 3H), 1.40 (m, 2H), 1.58 (m, 2H), 3.38 (m, 2H), 3.69 (s, 3H), 3.79 (s, 3H), 5.17 (s, 2H), 6.26 (s, 1H), 7.18 (m, 1H), 7.34 (m, 2H), 7.48 (m, 1H), 7.58 (s, 1H).

Compound 706: m.p. 92-94° C. δ(ppm): 0.94 (d 6H), 1.88 (m, 1H), 3.24 (t, 2H), 3.69 (s, 3H), 3.80 (s, 3H), 5.29 (s, 2H), 6.26 (s, 1H), 7.18 (m, 1H), 7.34 (m, 2H), 7.50 (m, 1H), 7.58 (s, 1H).

Compound 707: thick oil. δ(ppm): 0.99 (t, 3H), 1.25 (d, 3H), 1.69 (m, 2H), 3.68 (s, 3H), 3.80 (s, 3H), 4.30 (m, 1H), 5.34 (s, 2H), 6.17 (s, 1H), 7.20-7.24 (m, 1H), 7.34-7.40 (m, 2H), 7.48-7.51 (m, 1H), 7.62 (s, 1H).

Compound 708: thick oil. δ(ppm): 1.34 (t, 9H), 3.68 (s, 3H), 3.80 (s, 3H), 4.07 (m, 2H), 5.34 (s, 2H), 6.40 (s, 1H), 7.19-7.20 (m, 1H), 7.33-7.38 (m, 2H), 7.48-7.51 (m, 1H), 7.56 (m, 1H).

Compound 709: m.p. 93-95° C. δ(ppm): 1.59 (m, 4H), 1.62 (m, 2H), 3.68 (s, 3H), 3.77 (m, 4H), 3.84 (s, 3H), 5.27 (s, 2H), 6.17 (s, 1H), 7.19 (m, 1H), 7.34 (m, 2H), 7.48 (m, 1H), 7.56 (s, 1H).

Compound 710: m.p. 142-144° C. δ(ppm): 3.68 (s, 3H), 3.75 (m, 8H), 3.81 (s, 3H), 5.28 (s, 2H), 6.27 (s, 1H), 7.19 (m, 1H), 7.35 (m, 2H), 7.46 (m, 1H), 7.57 (s, 1H).

Compound 711: thick oil. δ(ppm): 1.25 (d, 6H), 2.59 (m, 2H), 3.60 (m, 2H), 3.68 (s, 3H), 3.80 (s, 3H), 4.53 (m, 2H), 5.28 (s, 2H), 6.24 (s, 1H), 7.19 (m, 1H), 7.35 (m, 2H), 7.49 (m, 1H), 7.56 (s, 1H).

Compound 715: m.p. 115-116° C.

FORMULATION EXAMPLE Base on 100% active ingredient (Weight/Weight %) Example 4 30% Compound 20 wettable powders

Compound 20 30%  Sodium dodecyl sulfate 2% Lignin sulfonate 3% Naphthalene sulfonic acid formaldehyde condensate 5% Precipitated calcium carbonate Make up to 100%

Compound 20 and other components are fully mixed, after smashing through ultrafine pulverizer, that is, 30% compound 20 wettable powders products.

Example 5 30% Compound 20 suspension concentrate

Compound 20 40% Glycol 10% Nonylphenols polyethylene glycol ether  6% Lignin sulfonate 10% Carboxymethyl cellulose  1% 37% formaldehyde aqueous solution 0.2%  75% of silicone oil water emulsion 0.8%  Water make up to 100%

Fully mixing the compound 20 and other components, suspension concentrate can be obtained, water suspension can be diluted from the concentration of any necessary dilution.

Example 6 60% Compound 20 water dispersible granules

Compound 20 60%  Naphthalene sulfonate formaldehyde condensate 12%  Sodium-N-methyl-N-oleyl taurate 8% Polyvinylpyrrolidone 2% Carboxymethyl cellulose 2% Kaolin make up to 100%

To mix the compound 20 and other components, after smashing, kneading together with water, added to the granulation 10-100 mesh machine for granulation, then by drying and sieving (at the scope screen).

BIOLOGICAL TESTING Example 7 Determination of Insecticidal and Acaricidal Activity

Determination of insecticidal and acaricidal activity of selected compounds were carried out by following procedure:

Compounds were dissolved in mixed solvent (acetone: methanol=1:1), and diluted to required concentration with water containing 0.1% of Tween 80.

The second instar larvae of armyworm (Spodoptera exigua), diamond backmoth (Plutella xylostella), green peach aphids (Myzus persicae) and mite (Tetranychus cinnabarinus) were used in biological test. The method was employed either spraying by airbrush. A test solution (0.5 ml) was sprayed at the pressure of 0.7 kg/cm². Percent mortality was determined after 2-3 days.

Part of Test Results:

At 600 mg/L, compound 25, 667 showed 100% control of diamond backmoth. Compound 229, 424, 475 showed 100% control of armyworm. Compounds 20, 25, 229, 682, 691, 693, 694, 697 showed 100% control of mite.

At 150 mg/L, compound 20 showed 100% control of mite.

At 40 mg/L, compound 691, 694, 701 showed 100% control of mite. Compound 682, 697 showed more than 95% control of mite.

At 5 mg/L, compound 20, 691, 694, 701 showed more than 50% control of mite.

At 10 mg/L, compound 20 showed 100% inhibition activity on carmine spider mite eggs. At 5 mg/L, compound 20 showed 80% inhibition activity on carmine spider mite eggs.

At 20 mg/L, compound 20 showed 100% control on nymph of carmine spider mite. At 10 mg/L, compound 20 showed 90% control on nymph of carmine spider mite.

Example 8 Determination of Fungicidal Activity

Determination of fungicidal activities against plant diseases of selected compounds were carried by following procedure:

Determination of Fungicidal Activity In Vitro:

Compounds were dissolved into DMSO to receive three solutions of 2000 mg/L, 667 mg/L and 222 mg/L for test. The solution for inhibition of fungal growth was added in 96 well polystyrene microtiter plates so that all wells receive 1 μl of DMSO solution of test compound, then 79 μl fungus conidial suspension were added into wells to receive the required concentration 25 mg/L, 8.3 mg/L and 2.8 mg/L respectively, which were placed into incubator. After 24 hours incubation, all plates were evaluated for inhibition percent of fungal growth.

Determination of Fungicidal Activity In Vivo:

Compounds were disolved into acetone to receive stock solution. Deionized water containing 0.1% Tween 80 was added in the previous solution to receive 20 ml test solution. Plants are sprayed by using a turntable sprayer. After 24 hours, plants were innoculated with a conidial suspension. Plants were then transferred into a dew chamber [R.H. (relative humidity)>95%] for infection. After this treatment, plants were removed from the chamber to the greenhouse for normal maintaining, After the infection period, the plants were placed in the greenhouse. After 1 week, the plants were scored for disease control.

Part of Test Results In Vitro:

At 25 mg/L, compound 19, 20, 25, 41, 232, 475, 664, 667, 668 showed 100% control of rice blast, compound 19, 20, 25, 41, 229, 232, 424, 664, 667, 668 showed 100% control of tomato late blight, compound 19, 20, 41, 667, 668 showed more than 50% control of cucumber grey mold.

At 8.3 mg/L, compound 19, 20, 666, 667, 676, 677 showed 100% control of rice blast, compound 25, 41, 229, 232, 475, 664, 665, 668, 670 showed about 80% control of rice blast.

At 2.8 mg/L, compound 19, 20 showed 100% control of rice blast, compound 41, 667, 676 showed about 80% control of rice blast, compound 667 showed about 50% control of cucumber grey mold.

Part of Test Results In Vivo:

At 400 mg/L, compound 19, 20, 25, 41, 229, 232, 424, 664, 667, 668 showed 100% control of cucumber downy mildew, compound 19, 20, 25, 41, 232, 424, 667, 668 showed 100% control of cucumber anthracnose, compound 680 showed 100% control of wheat powdery mildew, compound 19, 20, 25 showed more than 80% control of wheat powdery mildew.

At 25 mg/L, compound 19, 25, 41 showed 100% control of cucumber downy mildew, compound 19, 20, 25, 41, 665, 677, 669, 670, 678 showed 100% control of cucumber anthracnose, compound 680 showed 98% control of wheat powdery mildew, compound 19, 25, 41, 665, 669 showed 100% control of corn rust.

At 6.25 mg/L, compound 25, 665, 666, 667, 669, 678 showed more than 80% control of corn rust. 

1. Substituted pyrimidine ether compounds characterized with general formula I:

wherein: R₁ and R₂ may be the same or different, selected from H, CN, C₁-C₁₂haloalkyl, C₁-C₁₂ alkoxy, C₁-C₁₂haloalkoxy, C₃-C₆cycloalkyl, C₁-C₁₂ cyanoalkyl, C₁-C₁₂ allylamino, C₁-C₁₂haloalkylamino, C₂-C₆dialkylamino, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkyl carbonyl, C₁-C₁₂halo alkylsulfonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂halo alkoxyC₁-C₁₂ allyl, 2,3-(methylenedioxy)phenyl, 3,4-(methylenedioxy)phenyl, 2,3-(difluoromethylenedioxy)phenyl, 3,4-(difluoromethylenedioxy)phenyl, 2,3-dihydro-1H-indoline-4-yl, 5,6,7,8-tetrahydronaphthalene-1-yl, phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl or heteroaromatic rings; each phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl and heteroaromatic ring optionally substituted with 1-5 substituents independently selected from the group consisting of halogen, NO₂, CN, CONH₂, C₁-C₁₂alkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkenyloxy, C₂-C₁₂haloalkenyloxy, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₂-C₁₂alkynyloxy, C₂-C₁₂haloalkynyloxy, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkylamino, C₁-C₁₂halo alkylamino, C₂-C₆dialkylamino, C₁-C₁₂alkylcarbonylamino, C₁-C₁₂haloalkylcarbonylamino or R₅; Or NR₁R₂ can join together to form 5- or 6-membered ring; R₃ and R₄ may be the same or different, selected from H, halogen, NO₂, CN, C₁-C₁₂haloalkyl, C₃-C₆cycloalkyl, C₁-C₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂ alkylsulfonyl, C₁-C₁₂ alkylcarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂halo alkoxyC₁-C₁₂alkyl, phenyl, benzyl or hetero aromatic rings; each phenyl, benzyl and heteroaromatic ring optionally substituted with 1-5 substituents independently selected from the group consisting of halogen, NO₂, CN, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁ alkylthio, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl or R₃ and R₄ join together to form 5- or 6-membered ring; R₅ is selected from phenyl, benzyl, phenoxy or benzyloxy; each phenyl, benzyl, phenoxy and benzyloxy optionally substituted with 1-5 substituents independently selected from the group consisting of halogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy or C₁-C₆haloalkoxy; X is selected from O or S; Q is selected from one of the following group:

Or their salts.
 2. The compounds according to the claim 1, characterized in that wherein general formula I: R₁ and R₂ may be the same or different, selected from H, CN, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆halo alkoxy, C₃-C₆cyclo alkyl, C₁-C₆cyanoalkyl, C₁-C₆alkylamino, C₁-C₆haloalkylamino, C₂-C₆dialkylamino, C₁-C₆alkylthio, C₁-C₆allylsulfonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxyC₁-C₆allyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkoxycarbonylC₁-C₆alkyl, C₁-C₆halo alkoxyC₁-C₆alkyl, 2,3-(methylenedioxy)phenyl, 3,4-(methylenedioxy)phenyl, 2,3-(difluoromethylenedioxy)phenyl, 3,4-(difluoromethylenedioxy)phenyl, 2,3-dihydro-1H-indoline-4-yl, 5,6,7,8-tetrahydronaphthalene-1-yl, phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl, pyridyl, thienyl, thiazolyl, benzothiazolyl or pyrazolyl; each phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl, pyridyl, thienyl, thiazolyl, benzothiazolyl and pyrazolyl optionally substituted with 1-5 substituents independently selected from the group consisting of halogen, NO₂, CN, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆allylthio, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₃-C₆alkynyloxy, C₃-C₆haloalkynyloxy, C₁-C₆halo allylthio, C₁-C₆haloalkylcarbonyl, C₁-C₆alkylamino, C₁-C₆halo alkylamino, C₂-C₆dialkylamino, C₁-C₆alkylcarbonylamino, C₁-C₆haloalkylcarbonylamino or R₅; Or NR₁R₂ can join together to form morpholine, piperidine, pyrrolidine or piperazine; R₃ and R₄ may be the same or different, selected from H, halogen, NO₂, CN, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkoxycarbonylC₁-C₆allyl, C₁-C₆haloalkoxyC₁-C₆alkyl, phenyl, benzyl, pyridyl, thienyl, thiazolyl or pyrazolyl; each phenyl, benzyl, pyridyl, thienyl, thiazolyl and pyrazolyl optionally substituted with 1-3 substituents independently selected from the group consisting of halogen, NO₂, CN, C₁-C₆allyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylcarbonyl, C₁-C₆ alkoxycarbonyl or R₃ and R₄ join together to form 5- or 6-membered ring; R₅ is selected from phenyl, benzyl, phenoxy or benzyloxy; each phenyl, benzyl, phenoxy and benzyloxy optionally substituted with 1-5 substituents independently selected from the group consisting of: halogen, C₁-C_(a)alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy or C₁-C₃haloalkoxy; X is selected from O or S; Q is selected from one of the following group: Q₁-Q₁₄; Or their salts are formed with hydrochlorides, phosphates, acetic acid, benzenesulfonic acid or oxalic acid.
 3. The compounds according to the claim 2, characterized in that wherein general formula I: R₁ and R₂ may be the same or different, selected from H, CN, C₁-C₄alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ halo alkoxy, C₃-C₆ cyclo alkyl, C₁-C₃ cyanoalkyl, C₁-C₆alkylamino, C₁-C₃haloalkylamino, C₂-C₆dialkylamino, C₁-C₃allylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxyC₁-C₃ alkyl, C₁-C₃alkoxycarbonyl, C₁-C₃haloalkoxyC₁-C₃alkyl, phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl, pyridyl, thienyl, thiazolyl or benzothiazolyl; each phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl, pyridyl, thienyl, thiazolyl and benzothiazolyl optionally substituted with 1-3 substituents independently selected from the group consisting of halogen, NO₂, CN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylcarbonyl or C₁-C₃alkoxycarbonyl; Or NR₁R₂ can join together to form morpholine, piperidine, pyrrolidine or piperazine; R₃ and R₄ may be the same or different, selected from H, Cl, Br, NO₂, CN, C₁-C_(a)alkyl, C₁-C_(a)halo allyl, C₃-C₆cyclo alkyl, C₁-C₃alkoxy, C₁-C₃halo alkoxy, C₁-C₃alkoxyC₁-C₃alkyl, C₁-C₃haloalkoxyC₁-C₃allyl, C₁-C₃ alkylthio, C₁-C₃alkylsulfonyl, phenyl, benzyl, pyridyl, thienyl, thiazolyl or pyrazolyl; each phenyl, benzyl, pyridyl, thienyl, thiazolyl and pyrazolyl optionally substituted with 1-3 substituents independently selected from the group consisting of halogen, NO₂, CN, C₁-C₃allyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃ alkylcarbonyl or C₁-C₃alkoxycarbonyl; X is selected from O or S; Q is selected from one of the following group: Q₁-Q₉; Or their salts are formed with hydrochlorides, phosphates, acetic acid, benzenesulfonic acid or oxalic acid.
 4. The compounds according to the claim 3, characterized in that wherein general formula I: R₁ is selected from H or C₁-C₄ alkyl; R₂ is selected from H, CN, C₁-C_(a)alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₃-C₆cycloalkyl, C₁-C₃cyanoallyl, C₁-C_(a)alkylamino, C₁-C₃haloalkylamino, C₂-C₆dialkylamino, C₁-C₃alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxyC₁-C₂alkyl, phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl, pyridyl, thiazolyl or benzothiazolyl; each phenylcarbonyl, benzylcarbonyl, phenylamino, phenylaminocarbonyl, phenylcarbonylaminocarbonyl, phenyl, benzyl, pyridyl, thiazolyl and benzothiazolyl optionally substituted with 1-3 substituents independently selected from the group consisting of halogen, NO₂, CN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃allylthio or C₁-C₃alkoxycarbonyl; Or NR₁R₂ can join together to form morpholine, piperidine, pyrrolidine or piperazine; R₃ is selected from H, Cl, Br, F, C₁-C₄alkyl, C₃-C₆cycloalkyl, CF₃, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkoxyC₁-C₃alkyl, C₁-C₃haloalkoxyC₁-C₃alkyl, phenyl or pyridyl; each phenyl and pyridyl optionally substituted with 1-3 substituents independently selected from the group consisting of Cl, Br, F, NO₂, CN, C₁-C₃alkoxy or C₁-C₃haloalkoxy; R₄ is selected from H, Cl, Br, F, OCH₃, OCF₃, SCH₃, SO₂CH₃, NHCH₃, CH₃, CN, OCH₂CF₃, CO₂C₂H₅, phenyl, benzyl or pyridyl; each phenyl, benzyl and pyridyl optionally substituted with 1-3 substituents independently selected from the group consisting of Cl, Br, F, NO₂, CN, C₁-C₃alkyl, CF₃, C₁-C₃alkoxy or C₁-C₃ alkylthio; X is selected from O or S; Q is selected from one of the following group: Q₁-Q₅; Or their salts are formed with hydrochlorides, phosphates, acetic acid, benzenesulfonic acid or oxalic acid.
 5. The compounds according to the claim 4, characterized in that wherein general formula I: R₁ is selected from H or C₁-C₄ alkyl; R₂ is selected from H, CN, C₁-C₄alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₃-C₆cycloalkyl, phenyl, benzyl, pyridyl, thiazolyl or benzothiazolyl; each phenyl, benzyl, pyridyl, thiazolyl and benzothiazolyl optionally substituted with 1-3 substituents independently selected from the group consisting of Cl, Br, F, NO₂, CN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy or C₁-C₃haloalkoxy; Or NR₁R₂ can join together to form morpholine, piperidine, pyrrolidine or piperazine; R₃ is selected from H, Cl, Br, F, C₁-C₄alkyl, cyclopropyl, CF₃, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃ alkoxyC₁-C₃alkyl or C₁-C₃haloalkoxy C₁-C₃alkyl; R₄ is selected from H, Cl, Br, F, CH₃, OCH₃ or CN; X is selected from O or S; Q is selected from one of the following group: Q₁-Q₅.
 6. According to the claim 1, a use of the compounds having general formula I characterized with insecticidal, acaricidal and fungicidal activities used in agricultural and other fields.
 7. A composition of insecticides, acaricides and fungicides comprises, characterized in that the compounds having general formula I as an active ingredient, wherein the weight percentage of the active ingredient in the composition is from 0.5-90%. 